Dimethyl Sulfoxide → HCID 22492944, compound
Reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][O:12][CH:13]1[CH2:18][CH2:17][CH:16]([CH:19]2[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]2)[CH2:15][CH2:14]1.[Cl-].[NH4+]>ClCCl.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:11][O:12][CH:13]1[CH2:14][CH2:15][CH:16]([CH:19]2[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]2)[CH2:17][CH2:18]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- -78 °C
Procedure
A solution of oxalyl chloride (2.14 ml) in dichloromethane (80 ml) was cooled to −78° C. in nitrogen atmosphere, and a solution of dimethylsulfoxide (6 ml) in dichloromethane (6 ml) was added slowly and stirred for 10 minutes at −78° C. To the reaction mixture was added a solution of 4′-methoxy-1,1′-bi(cyclohexyl)-4-ol (2.6 g) in dichloromethane (26 ml) slowly to maintain the reaction temperature and stirred for 2.5 hours at −40° C. To the reaction mixture was added triethylamine (12.4 ml) slowly. Then the reaction mixture allowed to warm to room temperature. To the reaction mixture was added ammonium chloride solution and ethyl acetate. The organic layer was taken and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure to give 4′-methoxy-1,1′-bi(cyclohexyl)-4-one (1.62 g).
Workup
- temperatureto maintain the reaction temperature
- stirringstirred for 2.5 hours at −40° C
- temperatureto warm to room temperature
- dry with materialdried over magnesium sulfate
- filtrationThe magnesium sulfate was filtered off
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-c4271c8b3d4e429eb55b8d246216ff6a
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06884774B2
Reaction notes
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