4,4'-Di-2,4-hexadienoxybenzophenone → 4,4'-Di-2,4-hexadienoxytrityl alcohol

Participants

Reaction Steps

Compound 35 (2.0 grams) was dissolved in THF (45 mL) and phenylmagnesium bromide (1.0M solution in THF; 10.6 mL, 10.6 mmol) was added to the solution. The reaction mixture was stirred at room temperature for 3 hours, and evaporated to dryness under vacuum. The residue was redissolved in dichloromethane and washed with a saturated solution of ammonium chloride, followed by water. The organic phase was dried (MgSO4), concentrated in vacuo and purified column chromatography (silica gel; hexane/CH2Cl2, 1/9) to afford 1.84 grams (77%) of compound 36 as a pale yellow solid. 1H NMR (300 MHz, DMSO-d6) δ1.73 (d, J=6.9 Hz, 6H), 4.54 (d, J=6.0 Hz, 4H), 5.68-5.80 (m, 4H), 6.02, 6.11 (m, 2H), 6.20-6.37 (m, 2H), 6.85 (d, J=6.9 Hz, 4H), 7.05 (d, J=7.0 Hz, 4H), 7.14-7.32 (m, 5H); Anal. Calcd for C31H32O3 (452.5920): C, 82.27; H, 7.13; Found: C, 82.30; H, 7.11.

Provenance & Evidence