99113-85-6 → HCID 67268960, compound
Reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([CH:12]=[O:13])[O:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1COCC1>[C:1]1([C:7]2[CH:8]=[C:9]([CH:12]([OH:13])[CH2:12][CH2:9][CH2:8][CH2:7][CH2:1][CH:2]=[CH2:3])[O:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
The resulting Grignard solution was added to a solution of 4-phenyl-2-furaldehyde (1 eq.) in THF at 0° C. under Ar and the mixture was stirred for 30 min. The reaction was quenched by slow addition of sat. aq. NH4Cl solution and the desired product was extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4) and concentrated under reduced pressure. The crude was purified by column chromatography eluting with 5% EtOAc/Petroleum ether to afford the desired alcohol. 1H NMR (300 MHz, CD3Cl3) δ: 7.65 (2H, d, J=7.3 Hz), 7.42 (2H, t, J=7.2 Hz), 7.25-7.15 (1H, m), 6.60 (1H, d, J=5.3 Hz), 6.30 (1H, d, J=5.3 Hz), 5.87-5.75 (1H, m), 5.05-4.89 (2H, m), 4.75-4.65 (1H, m), 2.15-2.05 (2H, m), 1.87-1.75 (2H, m), 1.45-1.35 (6H, m). MS (ES) C18H22O2 requires: 270 found: 271 (M+H)+.