Bromide ion → HCID 58424622, compound

Participants

Reaction Steps

To a solution of 6-bromo-4′-t-butylspiro[chroman-2,1′-cyclohexan]-4-one (2.155 g, 6.13 mmol) in anhydrous THF (20 mL) at −78° C. is added a solution of vinylmagnesiun bromide in THF (1 M, 9.2 mL, 9.2 mmol) dropwise within 30 min. The reaction temperature is allowed to warm to rt and stirred for another 2 h. The reaction is chilled to 0° C. and quenched with sat. aq. NH4Cl, and extracted with ethyl acetate (2×40 mL). The combined organic phases are washed with H2O and brine, then dried over Na2SO4, and filtered. The filtrate is concentrated and the residue is purified through flash chromatography on silica gel to afford 6-bromo-4′-tert-butyl-4-vinylspiro[chroman-2,1′-cyclohexan]-4-ol as an oil (1.907 g, 82%). MS ESI+ve m/z 361 (M+H—H2O)+.

Provenance & Evidence