ChemicalBook CAS DataBase List 7-fluorochroman-4-ol

7-fluorochroman-4-ol synthesis

5synthesis methods

Product Name:7-fluorochroman-4-ol
CAS Number:917248-49-8
Molecular formula:C9H9FO2
Molecular Weight:168.16

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Yield:917248-49-8 74%

Reaction Conditions:

Stage #1: 3,4-dihydro-7-fluoro-2H-1-benzopyran-4-onewith sodium tetrahydroborate in methanol at 0; for 1 h;
Stage #2: with water in methanol;

Steps:

2.1

STEP 1 : 7-Fluorochroman-4-ol; To a solution of 7-fluoro-2,3-dihydro-4H-chromen-4-one (6.25 g, 37.6 mmol, US 20050038032) in methanol (60 mL) was added sodium borohydride (1.57 g, 41.4 mmol) at 0 ⁰C. The reaction mixture was stirred at the same temperature for 1 hour, and evaporated to remove methanol. The residue was EPO quenched with water, and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and concentrated in vacuum. The residue was purified by column chromatography on silica gel (hexane : ethyl acetate = 3 : 1 as an eluent) to afford the title compound as a pale gray solid (4.70 g, 74%): ¹H NMR (CDCI₃) δ: 7.35-7.22 (m, 1 H), 6.70-6.50 (m, 2H), 4.83-4.72 (m, 1 H), 4.27 (dd, J = 7.3, 3.7 Hz, 2H), 2.18-1.90 (m, 3H) ppm.

References:

WO2006/134460,2006,A1 Location in patent:Page/Page column 47-48