(1-(4-Fluorobenzyl)-5-methanesulfonylindol-2-yl)-methanol → 1-(4-Fluorobenzyl)-5-methanesulfonylindole-2-carbaldehyde

HRID 1814109

반응식

HRID 1814109 반응식
[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:13][CH:14]=3)[CH:9]=[C:8]2[CH2:20][OH:21])=[CH:4][CH:3]=1>ClCCl.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([S:16]([CH3:19])(=[O:17])=[O:18])=[CH:13][CH:14]=3)[CH:9]=[C:8]2[CH:20]=[O:21])=[CH:4][CH:3]=1

참가 물질

4

반응물 1

HCID 22504394(1-(4-Fluorobenzyl)-5-methanesulfonylindol-2-yl)-methanol

생성물 1

HCID 225043741-(4-Fluorobenzyl)-5-methanesulfonylindole-2-carbaldehyde수율 88.4%

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of lithium aluminum hydride (366 mg) in tetrahydrofuran (20 ml), a solution of 1-(4-fluorobenzyl)-5-methanesulfonylindole-2-carboxylic acid methyl ester obtained in Example 27 (3) (1.86 g) in tetrahydrofuran (20 ml) was added dropwise at 0° C. under nitrogen atmosphere and the mixture was stirred at the same temperature for 30 minutes. The reaction solution was poured into water, filtered through Celite and extracted with chloroform. The organic layer was washed with water and dried. The solvent was distilled off under reduced pressure to obtain (1-(4-fluorobenzyl)-5-methanesulfonylindol-2-yl)-methanol (1.8 g). To a solution of the resulting alcohol (1.8 g) in dichloromethane (100 ml) was added manganese dioxide (15.3 g) at 15 to 30° C. and the mixture was stirred at the same temperature for 30 minutes. The reaction solution was filtered through Celite. The solvent was distilled off under reduced pressure to obtain 1.5 g (88.4%) of the desired product as a yellow powder.

후처리

  1. filtrationThe reaction solution was filtered through Celite
  2. distillationThe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-0e3f9ac92a32465a93156d53b64aa0ac
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06875770B2

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