Sodium potassium tartrate tetrahydrate → 4-(tert-Butyl-dimethyl-silanyloxy)-1-trifluoromethyl-cyclohexanecarbaldehyde
Reaction equation
CON(C)[C:4]([C:6]1([C:20]([F:23])([F:22])[F:21])[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].[H-].C([Al+]CC(C)C)C(C)C.O.O.O.O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1COCC1.C(Cl)Cl>[C:16]([Si:13]([CH3:15])([CH3:14])[O:12][CH:9]1[CH2:10][CH2:11][C:6]([C:20]([F:23])([F:21])[F:22])([CH:4]=[O:5])[CH2:7][CH2:8]1)([CH3:19])([CH3:18])[CH3:17]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
4.15 g (11.2 mmol) of 4-(tert-Butyl-dimethyl-silanyloxy)-1-trifluoromethyl-cyclohexanecarboxylic acid methoxy-methyl-amide (70) were dissolved in 40 ml of anhydrous THF. Afterwards, 28.1 ml (28.1 mmol) of a 1M solution of diisobutylaluminium hydride in CH2Cl2 was added at 0° C. and the mixture was stirred at 0° C. for 30 minutes. 40 ml of a 10% aqueous solution of potassium sodium tartrate tetrahydrate were added and the mixture was stirred for 1 h at ambient temperature. The reaction mixture was then extracted twice using 50 ml of ethyl acetate each. The organic layer was dried over MgSO4 and evaporated to give 3.40 g of 71. Rt=0.98 min (Method Q).
Workup
- stirringthe mixture was stirred for 1 h at ambient temperature
- extractionThe reaction mixture was then extracted twice
- dry with materialThe organic layer was dried over MgSO4
- customevaporated
Sources & evidence
- ORD record
- ord-368239ae006741b0aade4b75991d4231
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399482B2
Reaction notes
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