Water → HCID 57517505, compound

HRID 2368125Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[Si:7]([O:24][CH:25]1[CH2:30][CH2:29][CH:28]([C:31](OCC)=[O:32])[CH2:27][CH2:26]1)([C:20]([CH3:23])([CH3:22])[CH3:21])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C1COCC1>[Si:7]([O:24][CH:25]1[CH2:26][CH2:27][CH:28]([CH2:31][OH:32])[CH2:29][CH2:30]1)([C:20]([CH3:23])([CH3:22])[CH3:21])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of lithium aluminum hydride (1.13 g) in THF (100 mL) was slowly added a solution of ethyl 4-{[tert-butyl(diphenyl)silyl]oxy}cyclohexanecarboxylate (12.2 g) in THF (100 mL) under ice-cooling. The reaction mixture was stirred at 0° C. for 1 hr, and water (1.2 mL) and 1M aqueous sodium hydroxide solution (1.2 mL) were successively added thereto. The mixture was stirred at room temperature for 30 min, and water (3.6 mL) was further added thereto. The mixture was stirred at room temperature for 1 hr, and the insoluble material was filtered off through celite under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (9.38 g).

Workup

temperaturecooling
stirringThe mixture was stirred at room temperature for 30 min
stirringThe mixture was stirred at room temperature for 1 hr
filtrationthe insoluble material was filtered off through celite under reduced pressure
customThe obtained residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-ec22dd554b694e72af74d513ea672ab1
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703758B2

Reaction notes

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