Ammonium Chloride → (1-benzenesulfonyl-1H-indol-6-yl)-methanol

HRID 74471Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[CH:19]=[C:18]2[C:14]([CH:15]=[CH:16][N:17]2[S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:22])=[O:21])=[CH:13][CH:12]=1)=O.[Cl-].[NH4+]>O1CCCC1>[C:23]1([S:20]([N:17]2[C:18]3[C:14](=[CH:13][CH:12]=[C:11]([CH2:9][OH:8])[CH:19]=3)[CH:15]=[CH:16]2)(=[O:21])=[O:22])[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A predetermined amount of lithium aluminum hydride (167 mg, 4.42 mmol) was placed into a reaction container, and anhydrous tetrahydrofuran (THF) (15 ml) was added thereto, and this was cooled to 0° C. An anhydrous tetrahydrofuran (THF) solution (5 ml) of 1-benzenesulfonyl-1H-indole-6-carboxylic acid methyl ester (930 mg, 2.95 mmol) was added to the mixture. This was stirred at 0° C. for 30 minutes. An aqueous solution saturated with ammonium chloride (1 ml) was added to the mixture. After Celite filtration, the Celite was washed with dichloromethane. The filtrate was dried over anhydrous sodium sulfate. The desiccant was removed by filtration, and concentration was performed. Then, by concentration under reduced pressure, (1-benzenesulfonyl-1H-indol-6-yl)-methanol was obtained as an oily brown material (859 mg, 100%).

Workup

additionwas added
filtrationAfter Celite filtration
washthe Celite was washed with dichloromethane
dry with materialThe filtrate was dried over anhydrous sodium sulfate
customThe desiccant was removed by filtration, and concentration
concentrationThen, by concentration under reduced pressure

Sources & evidence

ORD record: ord-3be38a671910443e9cbcc8fcbfc14d21
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829199B2

Reaction notes

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