Tetrahydrofuran → HCID 57705690, 화합물

반응식

[CH3:1][C:2]1([CH3:27])[C:7]([C:8]2[CH:13]=[C:12]([C:14](OC)=[O:15])[CH:11]=[CH:10][C:9]=2[C:18]2[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:19]=2[F:26])=[CH:6][CH2:5][CH2:4][CH2:3]1.C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>>[CH3:1][C:2]1([CH3:27])[C:7]([C:8]2[CH:13]=[C:12]([CH2:14][OH:15])[CH:11]=[CH:10][C:9]=2[C:18]2[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:19]=2[F:26])=[CH:6][CH2:5][CH2:4][CH2:3]1

참가 물질

반응물 4

HCID 8028Tetrahydrofuran2회

HCID 14798Sodium Hydroxide

HCID 21226445Aluminium lithium hydride

HCID 57706936[1,1′-Biphenyl]-4-carboxylic acid, 2-(6,6-dimethyl-1-cyclohexen-1-yl)-2′-fluoro-5′-methoxy-, methyl ester

생성물 1

HCID 57705690HCID 57705690, 화합물수율 90.2%

실험 절차

To a stirred solution of 66.21C (0.300 g, 0.814 mmol) in THF (0.0587 g, 0.814 mmol) at 0° C. was added LAH in THF (1.63 mL, 1.63 mmol, 1.0M). The reaction was stirred for 4.5 hours and then 1N NaOH(aq) was added to quench the mixture. The reaction was extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-20% EtOAc in hexanes) to yield 66.21D as a colorless oil (0.250 g, 90.2% yield).