Dimethyl Sulfoxide → HCID 17989195, compound

HRID 1444533Notes

Reaction equation

HRID 1444533 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][O:12][C:13]1[C:18]([C:19]([CH3:30])([CH3:29])[CH2:20][C:21]([OH:28])([CH2:26][OH:27])[C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:31][C:32]#[N:33].C(N(CC)CC)C>ClCCl.O>[CH3:11][O:12][C:13]1[C:18]([C:19]([CH3:30])([CH3:29])[CH2:20][C:21]([OH:28])([CH:26]=[O:27])[C:22]([F:23])([F:25])[F:24])=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:31][C:32]#[N:33]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 17989246HCID 17989246, compound

Product 1

HCID 17989195HCID 17989195, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

0.26 ml (2.99 mmol) of oxalyl chloride is cooled in 6.6 ml of dichloromethane to −78° C. After dropwise addition of 0.42 ml (5.98 mmol) of dimethyl sulfoxide, dissolved in 1.2 ml of dichloromethane, it is stirred for 10 more minutes and then 900 mg (2.72 mmol) of [2-methoxy-3-(4,4,4-trifluoro-3-hydroxy-3-hydroxymethyl-1,1-dimethylbutyl)phenyl]acetonitrile in 2.6 ml of dichloromethane is added in drops. After two hours of stirring at −78° C., 1.88 ml (13.58 mmol) of triethylamine is added in drops, the batch is allowed to come to room temperature, and then it is stirred for 1½ hours at room temperature. After mixing with water, it is extracted three times with dichloromethane. The combined organic extracts are washed with 1% sulfuric acid, with saturated sodium bicarbonate solution and with brine. After the solvent is dried and spun off, the residue is chromatographed on a Flashmaster. 599.4 mg (67.1%) of the desired aldehyde remains.

Workup

  1. stirringAfter two hours of stirring at −78° C.
  2. customto come to room temperature
  3. stirringit is stirred for 1½ hours at room temperature
  4. extractionis extracted three times with dichloromethane
  5. washThe combined organic extracts are washed with 1% sulfuric acid, with saturated sodium bicarbonate solution and with brine
  6. customAfter the solvent is dried
  7. customthe residue is chromatographed on a Flashmaster

Sources & evidence

ORD record
ord-8b212bd48fc04ab7b4736dfd22abec8f
Source dataset
uspto-grants-2010_02
Patent number
US07662821B2

Reaction notes

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