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

HRID 513858Notes

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-c082ef3a4bec444d8a302ff23cb2444b
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102692B2

Reaction notes

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