Tetrabutylammonium Fluoride → HCID 23498888, compound

Participants

Reaction Steps

To a solution of 4.0 g (7.7 mmol) of Methyl-4-{(E)-2-[3-(3-t-butyldimethylsiloxypropyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl]vinyl}benzoate in 20 mL tetrahydrofuran was added a solution of 8 mL (8.08 mmol) tetrabutylammonium fluoride (1.0 M in tetrahydrofuran). After 30 min the reaction mixture was diluted with water and extracted with ethyl acetate. The organic fraction was washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (ethyl acetate) to give 2.67 g (85%) of Methyl-4-{(E)-2-[3-(3-hydroxypropyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl]vinyl}benzoate (m.p.=109-115.5° C.).

Provenance & Evidence