ChemicalBook CAS DataBase List (3R)-8-hydroxy-6-methoxy-3-methyl-isochroman-1-one

(3R)-8-hydroxy-6-methoxy-3-methyl-isochroman-1-one synthesis

6synthesis methods

Product Name:(3R)-8-hydroxy-6-methoxy-3-methyl-isochroman-1-one
CAS Number:13410-15-6
Molecular formula:C11H12O4
Molecular Weight:208.21

(R)-3,4-Dihydro-6,8-dimethoxy-3-methyl-1H-2-benzopyran-1-one

15766-71-9
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(3R)-8-hydroxy-6-methoxy-3-methyl-isochroman-1-one

13410-15-6
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Yield: 70%

Reaction Conditions:

with boron trichloride in n-heptane;dichloromethane at -10; for 2 h;

Steps:

4.2.4. (R)-8-hydroxy-6-methoxy-3-methylisochroman-1-one (6-methoxymellein) 3
To the solution of valerolactone 16a (0.22g, 1 mmol) in anhydrous DCM was added BCl3 (1.2 mL, 1.2 mmol, 1 M in heptane) at _10 °C and reaction mixture was stirred for 2 h, and then quenched with sat. NaHCO3 and extracted with DCM (3 x 15 mL) and concentrated on rotavapour. The crude was purified by silica gel chromatography in hexane: EtOAc (65:35) afforded 6-methoxymellein 3 as white solid (0.159 g, 70% yield). mp 76-77 °C, [a]20 D _54 (c, 0.5), lit.[9g] [a]20 D _55 (c 0.23, MeOH); 1H NMR (400 MHz, CDCl3) d 11.25 (s, 1H), 6.37 (d, J 4 Hz, 1H), 6.26 (d, J 4 Hz, 1H), 4.67 (dd, J 13.9, 6.8 Hz, 1H), 3.83 (s, 3H), 2.87 (d, J 7.2 Hz, 2H); 1.51 (d, J 4 Hz, 3H) 13C NMR (101 MHz, CDCl3) d 169.8, 165.8, 164.5, 140.9, 106.1, 101.5, 99.4, 75.5, 55.5, 34.8, 20.6; HRMS (ESI+)[M+Na]+: found 231.0618C11H12NaO4 + requires 231.0628.

References:

Mane, Baliram B.;Markad, Sachin B.;Waghmode, Suresh B. [Tetrahedron,2020,vol. 76,# 46,art. no. 131524]