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(5‐methyl‐1,2‐oxazol‐3-yl)(oxan-4‐yl)methanol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
36%
Step 1: (5-Methyl-i ,2-oxazol-3-yl)(oxan-4-yl)methanol4-Bromooxane (270 jiL, 2.42 mmol) was added drop wise to a stirred suspension of magnesium (58.9 mg, 2.42 mmol) and one crystal of iodine in THF (1700 jiL) at ambient temperature. The reaction mixture was stirred for 1 h before 5-methyl-i ,2 - oxazole-3-carbaldehyde (119 jiL, i.28 mmol) was added in a single portion. The reaction mixture was then stirred for 16 h. The reaction mixture was quenched with a minimumamount of saturated aqueous ammonium chloride (5 mL), and the volatiles were removed under reduced pressure. The crude reaction material was purified using reverse phase preparatory HPLC (TFA/acetonitrile/water). (5-Methyl-i ,2 -oxazol-3 -yl)(oxan-4- yl)methanol (90.9 mg, 0.461 mmol, 36 %) was isolated as a colorless oil. LC/MS (M+H) = 198.2; LC/MS RT = 0.84 mm (Column: Phenomenex Luna 30 x 2.0 mm 3u; MobilePhase A: 10:90 acetonitrile:water with 0.1% TFA; Mobile Phase B: 90:10 acetonitrile:water with 0.1% TFA; Temperature: 40 C; Gradient: 0-100% B over 2 mm; Flow: 1 mL/min).
36%
With iodine; magnesium; In tetrahydrofuran; at 20℃; for 17h;
4-Bromooxane (270 μL, 2.42 mmol) was added drop wise to a stirred suspension of magnesium (58.9 mg, 2.42 mmol) and one crystal of iodine in THF (1700 μL) at ambient temperature. The reaction mixture was stirred for 1 h before <strong>[62254-74-4]5-methyl-1,2-oxazole-3-carbaldehyde</strong> (119 μL, 1.28 mmol) was added in a single portion. The reaction mixture was then stirred for 16 h. The reaction mixture was quenched with a minimum amount of saturated aqueous ammonium chloride (5 mL), and the volatiles were removed under reduced pressure. The crude reaction material was purified using reverse phase preparatory HPLC (TFA/acetonitrile/water). (5-Methyl-1,2-oxazol-3-yl)(oxan-4-yl)methanol (90.9 mg, 0.461 mmol, 36%) was isolated as a colorless oil. LC/MS (M+H)=198.2; LC/MS RT=0.84 min (Column: Phenomenex Luna 30×2.0 mm 3 u; Mobile Phase A: 10:90 acetonitrile:water with 0.1% TFA; Mobile Phase B: 90:10 acetonitrile:water with 0.1% TFA; Temperature: 40 C.; Gradient: 0-100% B over 2 min; Flow: 1 mL/min).
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