Diisobutylaluminum hydride → HCID 54756895, compound

Participants

Reaction Steps

DIBAL-H (20% w/w in toluene, 2 mL, 2.39 mmol) was added to a slurry of ester 100 (0.396 g, 1.23 mmol) in toluene (12 mL) at −78° C. The mixture was warmed to room temperature, stirred for 1 h, and then poured onto ice cold NH4Cl solution (50 mL). The mixture was diluted with CH2Cl2 (100 mL), filtered through Celite and the organic layer was dried and evaporated. Column chromatography of the residue on silica gel using gradient elution (CH2Cl2 to 95:5 CH2Cl2:EtOAc) gave (2E)-3-[4′-(trifluoromethoxy)[1,1′-biphenyl]-4-yl]-2-propen-1-ol (101) (0.195 g, 54%) as a white solid: mp 121-123° C.; NMR (CDCI3) δ 7.60 (d, J=8.7 Hz, 2H), 7.53 (d, J=8.4 Hz, 2H), 7.47 (d, J=8.4 Hz, 2H), 7.28 (d, J=8.1 Hz, 2H), 6.66 (d, J=15.9 Hz, 1H), 6.42 (dt, J=15.9, 5.7 Hz, 1H), 4.36 (dd, J=5.9, 5.7 Hz, 2H), 1.44 (t, J=5.9 Hz, 1H). APCI MS m/z 307 [M−H−H2O+MeOH]−.

Provenance & Evidence