Tetrahydrofuran → HCID 57705690、化合物

反応式

[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

参加物

反応物 4

HCID 8028Tetrahydrofuran

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

生成物 1

HCID 57705690HCID 57705690、化合物収率 90.2%

実験手順

To a stirred solution of T12.6 (0.300 g, 0.814 mmol) in THF (0.0587 g, 0.814 mmol) at 0° C. was added LAH (1.63 mL, 1.63 mmol, 1.0M). The resulting mixture was stirred for 4.5 hours. Next, 1N NaOH(aq) was added to quench the mixture. The reaction was extracted three times with EtOAc. The combined organic layers were dried over anhydrous magnesium sulfate and filtered. The organic solvent was removed under reduced pressure, and the product was purified on silica gel (0-20% EtOAc in hexanes) to yield T12.7 as a colorless oil (0.250 g, 90.2% yield).