Diisopropylamine → 1-Cyclohexyl-1-phenyl-1-trimethylsilyloxy-2-propanone
Reaction equation
C(NC(C)C)(C)C.[Li]CCCC.C(OP(OCC)(C(O[Si:21]([CH3:24])([CH3:23])[CH3:22])C)=O)C.[C:28]1([C:34]([CH:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C1C[O:45][CH2:44][CH2:43]1>CCCCCC.O>[CH:28]1([C:34]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)([O:35][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:44](=[O:45])[CH3:43])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
To a stirred solution of 35 ml (0.25 mole) of diisopropylamine in 800 ml of THF at -78° C. was added 100 ml of a 2.5M solution of n-BuLi in hexane. After the mixture was stirred at -78° C. for 1 hour, 52 g (0.205 mole) of 1-(diethoxyphosphinyl)-1-trimethylsilyloxyethane [prepared according to the procedure of G. H. Birum and G. A. Richardson, U.S. Pat. No. 3,113,139 (1963)] was added dropwise. The mixture was stirred for 1.5 hours at -78° C. and then 42.5 g (0.225 mole) of cyclohexyl phenyl ketone in 100 ml of THF was added dropwise at -78° C. The stirred solution was warmed to room temperature during 30 minutes and then it was poured into 2 L of water. Extraction of the mixture with ether, after washing with dilute hydrochloric acid, drying and concentrating gave 51 g (75%) of colorless liquid.
Workup
- addition3,113,139 (1963)] was added dropwise
- stirringThe mixture was stirred for 1.5 hours at -78° C.
- temperatureThe stirred solution was warmed to room temperature during 30 minutes
- extractionExtraction of the mixture with ether
- washafter washing with dilute hydrochloric acid
- customdrying
- concentrationconcentrating
Sources & evidence
- ORD record
- ord-d65861a8a90b4ad78a9d07661cfa1ab8
- Source dataset
- uspto-grants-1991_07
- Patent number
- US05036107
Reaction notes
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