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

HRID 1838370

Reaction equation

HRID 1838370 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[N:12]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[C:13]2[C:18]([CH:19]=1)=[CH:17][C:16]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][CH:14]=2)=O.O>O1CCCC1>[F:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][N:12]2[C:13]3[C:18](=[CH:17][C:16]([S:20]([CH3:23])(=[O:21])=[O:22])=[CH:15][CH:14]=3)[CH:19]=[C:11]2[CH2:9][OH:8])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 684447041-(4-fluorobenzyl)-5-methanesulfonylindole-2-carboxylic Acid Methyl Ester

Product 1

HCID 22504394(1-(4-Fluorobenzyl)-5-methanesulfonylindol-2-yl)-methanolYield 104.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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

  1. filtrationfiltered through Celite
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with water
  4. customdried
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a5c7bf32bc3b4d2f9dd0f9ed0c7a4b35
Source dataset
uspto-grants-2004_01
Patent number
US06673797B1

Linked notes

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