Water → tert-Butyl (2E)-3-{4-[cyclohexylidene(4-hydroxyphenyl)methyl]-2-fluorophenyl}prop-2-enoate

Participants

Reaction Steps

A solution of (tert-butoxycarbonylmethylene)triphenylphosphorane (610 mg, 1.62 mmol) in CH2Cl2 (10 mL) was added dropwise to 89 (200 mg, 0.644 mmol) dissolved in CH2Cl2 (10 mL) at RT. After stirring for 2 h at RT, water (50 mL) was added and the mixture was extracted with CH2Cl2 (3×25 mL). The combined organic layers were washed with brine (50 mL) and dried over MgSO4. Concentration followed by flash chromatography (20:1 to 5:1 hexanes:EtOAc) and recrystallization (hexanes:EtOAc) afforded 180 mg (68%) of 90 as a white crystalline solid. 1H NMR (400 MHz, CDCl3): δ 1.52 (s, 9H), 1.59 (br s, 6H), 2.22 (br s, 4H), 5.24 (s, 1H), 6.40 (d, J=16.3 Hz, 1H), 6.76 (d, J=8.4 Hz, 2H), 6.80-6.89 (m, 2H), 6.94 (d, J=8.4 Hz, 2H), 7.37 (t, J=7.9 Hz, 1H), 7.67 (d, J=16.3 Hz, 1H).

Provenance & Evidence