Dimethyl Sulfoxide → HCID 19600233, compound

HRID 611404Notes

Reaction equation

HRID 611404 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[O:11]1[C:19]2[CH2:18][CH2:17][N:16]([S:20]([C:23]3[CH:30]=[CH:29][C:26]([CH2:27][OH:28])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH2:15][C:14]=2[CH:13]=[CH:12]1.C(N(CC)CC)C>ClCCl>[O:11]1[C:19]2[CH2:18][CH2:17][N:16]([S:20]([C:23]3[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH2:15][C:14]=2[CH:13]=[CH:12]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 54274472HCID 54274472, compound

Product 1

HCID 19600233HCID 19600233, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4.27 g (33.6 mmol) of oxalyl chloride in 100 ml of dichloromethane, 4.78 ml (67.3 mmol) of dimethyl sulfoxide was added dropwise at -78° C., followed by stirring for 5 minutes. To this solution, a solution of 6.580 g (22.431 mmol) of 4-(6,7-dihydro-4H-furo[3,2-c]pyridin-5-ylsulfonyl)benzyl alcohol in 50 ml of dichloromethane was added at -78° C., followed by stirring for 15 minutes. To this mixture, 18.8 ml (135 mmol) of triethylamine was added; the mixture was allowed to warm to room temperature. After the reaction mixture was washed with water, the water layer was re-extracted with diethyl ether. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=6/1 to 3/1 to 2/1) to yield the desired product.

Workup

  1. stirringby stirring for 15 minutes
  2. washAfter the reaction mixture was washed with water
  3. extractionthe water layer was re-extracted with diethyl ether
  4. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=6/1 to 3/1 to 2/1)

Sources & evidence

ORD record
ord-4169e760c610469ca3b06905e6718135
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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