Tetrabutylammonium Fluoride → HCID 57475780, compound

To a solution of 1-(3-bromophenyl)-1-(tert-butyldimethylsilyloxy)hex-5-en-3-ol (18.8 g, 44.0 mmol) in tetrahydrofuran (60 mL) is added 1 M tetrabutylammonium fluoride solution in THF (66.0 mL, 66.0 mmol). The resulting mixture is stirred at room temperature for 2 hours. The mixture is diluted with dichloromethane and is washed sequentially with water and saturated ammonium chloride aqueous solution. The organic layer is dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a residue. The crude product is purified by silica gel chromatography eluting with a linear gradient of 20% to 40% ethyl acetate in hexanes over 26 minutes to give the title compound as racemic diastereomeric mixture (11.8 g, 99%). 1H NMR (400 MHz, CDCl3) δ 7.52 (s, 1H), 7.38-7.36 (m, 1H), 7.28-7.24 (m, 1H), 7.22-7.17 (m, 1H), 5.83-5.75 (m, 1H), 5.15-5.11 (m, 2H), 5.03-4.89 (m, 1H), 4.00-3.90 (m, 1H), 2.32-2.21 (m, 2H), 1.96-1.89 (m, 2H).

1. washis washed sequentially with water and saturated ammonium chloride aqueous solution
2. dry with materialThe organic layer is dried over sodium sulfate
3. filtrationfiltered
4. concentrationconcentrated under reduced pressure
5. customto give a residue
6. customThe crude product is purified by silica gel chromatography
7. washeluting with a linear gradient of 20% to 40% ethyl acetate in hexanes over 26 minutes

ORD record

ord-70986de71a344574bd393266de18e383

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08278441B2