Ammonium Chloride → 10-(2-dimethylaminoethyl)-10,11-dihydro-5-trimethylsilylmethyl-5H-dibenzo[a,d]cyclohepten-5-ol
Reaction equation
[CH3:1][Si:2]([CH2:5]Cl)([CH3:4])[CH3:3].[Mg].[CH3:8][N:9]([CH3:28])[CH2:10][CH2:11][CH:12]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[C:16](=[O:23])[C:15]2[CH:24]=[CH:25][CH:26]=[CH:27][C:14]=2[CH2:13]1.[Cl-].[NH4+]>CCOCC>[CH3:28][N:9]([CH3:8])[CH2:10][CH2:11][CH:12]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[C:16]([CH2:5][Si:2]([CH3:3])([CH3:4])[CH3:1])([OH:23])[C:15]2[CH:24]=[CH:25][CH:26]=[CH:27][C:14]=2[CH2:13]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A Grignard reagent is prepared by conventional techniques from 12.2 g. (0.1 mole) trimethylsilylmethyl chloride and 24.3 g. magnesium metal (0.1 atom) and 200 ml. ether. The resulting solution is treated with 27.9 g. (0.1 mole) of 10-(2-dimethylaminoethyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one in 100 ml. ether. Stirring is initiated and the mixture is heated at reflux for 5 hours, then cooled in ice and hydrolyzed with 150 ml. of saturated ammonium chloride. The layers are separated and the ether dried over anhydrous magnesium sulfate and evaporated to give 10-(2-dimethylaminoethyl)-10,11-dihydro-5-trimethylsilylmethyl-5H-dibenzo[a,d]cyclohepten-5-ol.
Workup
- additionThe resulting solution is treated with 27.9 g
- temperaturethe mixture is heated
- temperatureat reflux for 5 hours
- temperaturecooled in ice and hydrolyzed with 150 ml
- customThe layers are separated
- dry with materialthe ether dried over anhydrous magnesium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-584dba3c22e04c119e4692954161535c
- Source dataset
- uspto-grants-1976_11
- Patent number
- US03994961
Reaction notes
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