Dimethyl Sulfoxide → HCID 22561004, compound
Reaction equation
CS(C)=O.[C:5](Cl)(=O)[C:6](Cl)=O.C(C1C=CC=CC=1[CH2:15][O:16][C:17](=[O:25])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24])#N.C([N:32]([CH2:35][CH3:36])CC)C>ClCCl>[C:35]([C:36]1[CH:6]=[CH:5][CH:17]=[CH:18][C:19]=1[CH2:20][CH:22]([CH:23]=[O:24])[CH2:21][CH2:20][CH2:19][CH2:18][C:17]([O:16][CH3:15])=[O:25])#[N:32]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -60 °C
Procedure
At −60° C., a solution of 49.37 mg (0.63 mmol) of dimethyl sulfoxide (DMSO) in 0.5 ml of dichloromethane was added dropwise to a solution of 40.10 mg (0.32 mmol) of oxalyl chloride in 2 ml of dichloromethane. The mixture was stirred at −60° C. for 15 min, and a solution of 58.00 mg (0.21 mmol) of methyl &(2-cyanobenzyl)-7-hydroxyheptanoate from Ex. XXIIId in 1 ml of dichloromethane was then added dropwise. The mixture was stirred at −60° C. for another 15 min, 106.58 mg (1.05 mmol) of triethylamine were added, the cooling bath was removed and the mixture was stirred for 2 h. Water was added, the mixture was extracted with dichloromethane, the combined organic phases were dried over Na2SO4, the solvent was removed and the crude product was dried under high vacuum. The resulting aldehyde could be used without further purification.
Workup
- stirringThe mixture was stirred at −60° C. for another 15 min
- customthe cooling bath was removed
- stirringthe mixture was stirred for 2 h
- additionWater was added
- extractionthe mixture was extracted with dichloromethane
- dry with materialthe combined organic phases were dried over Na2SO4
- customthe solvent was removed
- dry with materialthe crude product was dried under high vacuum
- customThe resulting aldehyde could be used without further purification
Sources & evidence
- ORD record
- ord-b3003e9544fc4d61b7f9e485ce8d795c
- Source dataset
- uspto-grants-2005_03
- Patent number
- US06864287B1
Reaction notes
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