(1-(4-Fluorobenzyl)-5-methanesulfonylindol-2-yl)-methanol → 1-(4-Fluorobenzyl)-5-methanesulfonylindole-2-carbaldehyde
Reaction equation
[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]=1Participants
Procedure
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.
Workup
- filtrationThe reaction solution was filtered through Celite
- distillationThe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-d8eb184d36e2452b952fa0b6b76326b6
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06673797B1
Reaction notes
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