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With sodium hydroxide In tetrahydrofuran; methanol; chloroform; water; ethyl acetate
C. 5-(Hydroxymethyl)thiazole To a precooled (ice bath) three neck 500 mL flask containing lithium aluminum hydride (2.89 g, 76 mmol) in 250 mL of THF was added ethyl thiazole-5-carboxylate (11.82 g, 75.68 mmol) in 100 mL of THF dropwise over 1.5 hours to avoid excess foaming. The reaction was stirred for an additional hour, and treated cautiously with 2.9 mL of water, 2.9 mL of 15percent NaOH, and 8.7 mL of water. The solid salts were filtered, and the filtrate set aside. The crude salts were heated at reflux in 100 mL of ethyl acetate for 30 minutes. The resulting mixture was filtered, and the two filtrates were combined, dried over Na2 SO4, and concentrated in vacuo. The product was purified by silica gel chromatography eluding sequentially with 0percent -2percent -4percent methanol in chloroform, to provide the desired compound, Rf-0.3 (4percent methanol in chloroform), which solidified upon standing in 75percent yield. NMR (CDCl3) δ4.92 (s, 2H), 7.78 (s, 1H), 8.77 (s, 1H). Mass spectrum: (M+H)+ =116.
75%
With sodium hydroxide In tetrahydrofuran; methanol; chloroform; water; ethyl acetate
P. 5-(Hydroxymethyl)thiazole To a precooled (ice bath) three neck 500 mL flask containing lithium aluminum hydride (76 mmol) in 250 mL of THF was added ethyl thiazole-5-carboxylate (11.82 g, 75.68 mmol) in 100 mL of THF dropwise over 1.5 hours to avoid excess foaming. The reaction was stirred for an additional hour, and treated cautiously with 2.9 mL of water, 2.9 mL of 15percent NaOH, and 8.7 mL of water. The solid salts were filtered, and the flitrate set aside. The crude salts were heated at reflux in 100 mL of ethyl acetate for 30 min. The resulting mixture was filtered, and the two filtrates were combined, dried over Na2 SO4, and concentrated in vacuo. The product was purified by silica gel chromatography eluding sequentially with 0percent -2percent-4percent methanol in chloroform, to provide the desired compound, Rf=0.3 (4percent methanol in chloroform), which solidified upon standing in 75percent yield. NMR (CDCl3)δ4.92 (s, 2H), 7.78 (s, 1H), 8.77 (s, 1H). Mass spectrum: (M+H)+ =116.
75%
With sodium hydroxide In tetrahydrofuran; methanol; chloroform; water; ethyl acetate
K. 5-(Hydroxymethyl)thiazole To a precooled (ice bath) three neck 500 mL flask containing lithium aluminum hydride (76 mmol) in 250 mL of THF was added ethyl thiazole-5-carboxylate (11.82 g, 75.68 mmol) in 100 mL of THF dropwise over 1.5 hours to avoid excess foaming. The reaction was stirred for an additional hour, and treated cautiously with 2.9 mL of water, 2.9 mL of 15percent NaOH, and 8.7 mL of water. The solid salts were filtered, and the filtrate set aside. The crude salts were heated at reflux in 100 mL of ethyl acetate for 30 min. The resulting mixture was filtered, and the two filtrates were combined, dried over Na2 SO4, and concentrated in vacuo. The product was purified by silica gel chromatography eluding sequentially with 0percent - 2percent - 4percent methanol in chloroform, to provide the desired compound, Rf=0.3 (4percent methanol in chloroform), which solidified upon standing in 75percent yield. NMR (CDCl3) δ4.92 (s, 2H), 7.78 (s, 1 H), 8.77 (s, 1H). Mass spectrum: (M+H)+ =116.
75%
With sodium hydroxide In tetrahydrofuran; methanol; chloroform; water; ethyl acetate
K. 5-(Hydroxymethyl)thiazole. To a precooled (ice bath) three neck 500 mL flask containing lithium aluminum hydride (76 mmol) in 250 mL of THF was added ethyl thiazole-5-carboxylate (11.82 g, 75.68 mmol) in 100 mL of THF dropwise over 1.5 hours to avoid excess foaming. The reaction was stirred for an additional hour, and treated cautiously with 2.9 mL of water, 2.9 mL of 15percent NaOH, and 8.7 mL of water. The solid salts were filtered, and the filtrate set aside. The crude salts were heated at reflux in 100 mL of ethyl acetate for 30 min. The resulting mixture was filtered, and the two filtrates were combined, dried over Na2 SO4, and concentrated in vacuo. The product was purified by silica gel chromatography eluding sequentially with 0percent-2percent-4percent methanol in chloroform, to provide the desired compound, Rf=0.3 (4percent methanol in chloroform), which solidified upon standing in 75percent yield. NMR (CDCl3) δ4.92 (s, 2H), 7.78 (s, 1H), 8.77 (s, 1H). Mass spectrum: (M+H)+ =116.
75%
With sodium hydroxide In tetrahydrofuran; methanol; chloroform; water; ethyl acetate
D. 5-(Hydroxymethyl)thiazole To a precooled (ice bath) three neck 500 mL flask containing lithium aluminum hydride (76 mmol) in 250 mL of THF was added ethyl thiazole-5-carboxylate (11.82 g, 75.68 mmol)in 100 mL of THF dropwise over 1.5 hours to avoid excess foaming. The reaction was stirred for an additional hour, and treated cautiously with 2.9 mL of water, 2.9 mL of 15percent NaOH, and 8.7 mL of water. The solid salts were filtered, and the filtrate set aside. The crude salts were heated at reflux in 100 mL of ethyl acetate for 30 min. The resulting mixture was filtered, and the two flitrates were combined, dried over Na2 SO4, and concentrated in vacuo. The product was purified by silica gel chromatography eluding sequentially with 0percent-2percent-4percent methanol in chloroform, to provide the desired compound, Rf=0.3 (4percent methanol in chloroform), which solidified upon standing in 75percent yield. NMR (CDCl3) δ4.92 (s, 2 H), 7.78 (s, 1 H), 8.77 (s, 1 H). Mass spectrum: (M+H)+ =116.
Reference：
[1] Journal of Medicinal Chemistry, 2017, vol. 60, # 7, p. 3124 - 3153
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 4, p. 602 - 617
[3] Patent: US5914332, 1999, A,
[4] Patent: US5455351, 1995, A,
[5] Patent: US5559158, 1996, A,
[6] Patent: US5484801, 1996, A,
[7] Patent: US5461067, 1995, A,
[8] Patent: EP1170289, 2002, A2, . Location in patent: Page 44-45
[9] Helvetica Chimica Acta, 1952, vol. 35, p. 215
[10] Journal of Medicinal Chemistry, 1973, vol. 16, p. 978 - 984
[11] Patent: US5559158, 1996, A,
[12] Patent: US5484801, 1996, A,
2
[ 14527-44-7 ]
[ 38585-74-9 ]
Yield
Reaction Conditions
Operation in experiment
69%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0℃; for 1 h; Stage #2: With sodium hydroxide In water at 0℃; for 0.5 h;
A mixture of 0. 54 g of g-4 and 10ml tetrahydrofurane (THF) was stirred at 0°C under a nitrogen atmosphere. The mixture of 0. 16g of lithium aluminium hydride and 5ml of ether was added drop wise. After lhour at 0°C water and 20percent sodium hydroxide were added, and stirred during 30 minutes. The mixture was filtered over decalite and the solvent was removed by azeotropique distillation with toluene yielding 0.3g (69percent) of thiazol-5-yl-methanol (g-5).
Reference：
[1] Patent: WO2003/97616, 2003, A1, . Location in patent: Page/Page column 26
[2] Patent: US5968942, 1999, A,
[3] Patent: US6046190, 2000, A,
3
[ 170232-68-5 ]
[ 38585-74-9 ]
Reference：
[1] Synthetic Communications, 1995, vol. 25, # 17, p. 2639 - 2645
[2] Synthetic Communications, 1995, vol. 25, # 24, p. 4081 - 4086
[3] Journal of Labelled Compounds and Radiopharmaceuticals, 2009, vol. 52, # 4, p. 110 - 113
4
[ 1003-32-3 ]
[ 38585-74-9 ]
Reference：
[1] Journal of Materials Chemistry, 2009, vol. 19, # 19, p. 2975 - 2985
[2] Journal of medicinal chemistry, 1998, vol. 41, # 26, p. 5265 - 5271
[3] Patent: US5780638, 1998, A,
[4] Patent: US2009/170907, 2009, A1, . Location in patent: Page/Page column 59
[5] Patent: WO2010/132999, 2010, A1, . Location in patent: Page/Page column 112
5
[ 145015-15-2 ]
[ 38585-74-9 ]
Reference：
[1] Patent: US5959118, 1999, A,
[2] Patent: US5773625, 1998, A,
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