Dimethyl Sulfoxide → 4-{[tert-Butyl(diphenyl)silyl]oxy}cyclohexane-1-carbonitrile
Reaction equation
[Si:1]([O:18][CH:19]1[CH2:24][CH2:23][CH:22]([C:25]([NH2:27])=O)[CH2:21][CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(C)=O.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C>C(Cl)Cl>[Si:1]([O:18][CH:19]1[CH2:20][CH2:21][CH:22]([C:25]#[N:27])[CH2:23][CH2:24]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 6.42 g of 4-((tert-butyl(diphenyl)silyl)oxy)cyclohexanecarboxamide and 2.39 ml of dimethylsulfoxide in 90 ml of methylene chloride was added a solution of 2.06 ml of oxalyl chloride in 10 ml of methylene chloride at −78° C., followed by stirring the reaction mixture at −78° C. for 15 minutes. To the reaction mixture was added 7.05 ml of triethylamine at −78° C., followed by stirring the reaction mixture at −78° C. for 30 minutes and then stirring at room temperature for 1.5 hours. The reaction mixture was washed with water and brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo. The obtained residue was purified by a silica gel column chromatography (eluent: hexane to hexane/ethyl acetate=4/1) to give the title compound as a pale yellow oil.
Workup
- stirringby stirring the reaction mixture at −78° C. for 30 minutes
- stirringstirring at room temperature for 1.5 hours
- washThe reaction mixture was washed with water and brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationThe filtrate was concentrated in vacuo
- customThe obtained residue was purified by a silica gel column chromatography (eluent: hexane to hexane/ethyl acetate=4/1)
Sources & evidence
- ORD record
- ord-da08dd9e6d5a4b6d9537dcf72756755e
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07915263B2
Reaction notes
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