Methyl 5-(hydroxymethyl)-2-methoxybenzoate synthesis

Yield:191604-81-6 68%

Reaction Conditions:

with sodium tetrahydroborate in tetrahydrofuran at 20; for 2 h;

Steps:

xxvi.a

a) Methyl 5-(hydroxymethyl)-2-methoxybenzoate I58 To a solution of methyl 5-formyl-2-methoxybenzoate (4.6 g, 23.7 mmol) in THF (230 ml.) was added NaBH4 (1.1 g, 28.4 mmol) and the mixture was stirred at room temperature for 2 h. The reaction was quenched with 1 M aqueous HCI then diluted with water and extracted with DCM. The organic extracts were washed with brine, dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Pet. Ether/DCM = 1/2) to give the title compound (3.2 g, 68%) as a yellow oil. LCMS-E (ES-API): Rt 0.77 min; m/z 197.0 [M+H]+.

References:

WO2020/2587,2020,A1 Location in patent:Page/Page column 79