Lithium hydroxide, monohydrate → 4-[(tert-Butyldimethylsilyl)oxy]cyclohexanecarboxylic Acid
Reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH2:8][CH2:7]1)=[O:5])C.O.[OH-].[Li+]>O1CCCC1.CO>[C:16]([Si:13]([CH3:15])([CH3:14])[O:12][CH:9]1[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]1)([CH3:19])([CH3:18])[CH3:17]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
To a solution of Example 45A (6.6 g, 23.0 mmol) in tetrahydrofuran (31 mL) and methanol (20 mL) was added lithium hydroxide monohydrate (1.93 g, 46.1 mmol). The resulting mixture was heated at 60° C. for 2 hours. The heat was removed and the reaction mixture was stirred at room temperature overnight. The solvents were removed in vacuo and the solution was neutralized with 1M HCl. Ethyl acetate (200 mL) was added and the layers were separated. The aqueous layer was further extracted with ethyl acetate (2×200 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated to give the titled compound (4.5 g). MS (CI) m/z 259 (M+1)+
Workup
- customThe heat was removed
- customThe solvents were removed in vacuo
- additionEthyl acetate (200 mL) was added
- customthe layers were separated
- extractionThe aqueous layer was further extracted with ethyl acetate (2×200 mL)
- dry with materialThe combined organic layers were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-03cdd37967844e49a3fe96e398de0f2e
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08119664B2
Reaction notes
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