Tetrahydrofuran → 1-(4-(1,3-Dioxolan-2-yl)phenyl)-2-phenylethanone

반응식

[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:13]=[CH:12][C:9]([C:10]#N)=[CH:8][CH:7]=1.[CH2:14]([Mg]Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1C[O:26]CC1>>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:13]=[CH:12][C:9]([C:10](=[O:26])[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8][CH:7]=1

참가 물질

반응물 3

HCID 8028Tetrahydrofuran

HCID 27784284-(1,3-Dioxolan-2-yl)benzonitrile

HCID 178418336HCID 178418336, 화합물

생성물 1

HCID 591643561-(4-(1,3-Dioxolan-2-yl)phenyl)-2-phenylethanone

실험 절차

To a solution of 4-(1,3-dioxolan-2-yl)benzonitrile (5.0 g, 28.54 mmol) in anhydrous THF (100 mL) was added benzyl magnesium chloride (36 mL, 20% wt solution in THF, 43 mmol) slowly at 0° C. After one hour the mixture was warmed to room temperature. After four hours the mixture was cooled to 0° C. and quenched with saturated NH4Cl. The mixture was warmed to room temperature and extracted with ethyl acetate (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column chromatography (10% ethyl acetate/hexanes) gave 1-[4-(1,3-dioxolan-2-yl)phenyl]-2-phenylethanone as a pale yellow solid: 1H-NMR (500 MHz, CDCl3): δ 8.02 (2H, d, J=8.30 Hz,), 7.57 (2H, d, J=8.30 Hz,), 7.38-7.24 (5H, m), 5.86 (1H, s), 4.29 (2H, s), 4.28-4.09 (4H, m).