Dimethyl Sulfoxide → HCID 19599906, compound

HRID 611406Notes

Reaction equation

HRID 611406 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:28]=[CH:27][C:26]([CH:29]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[OH:30])=[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>[C:29]([C:26]1[CH:25]=[CH:24][C:23]([S:20]([N:16]2[CH2:17][CH2:18][C:19]3[O:11][CH:12]=[CH:13][C:14]=3[CH2:15]2)(=[O:22])=[O:21])=[CH:28][CH:27]=1)(=[O:30])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19600247HCID 19600247, compound

Product 1

HCID 19599906HCID 19599906, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.16 ml (1.2 mmol) of oxalyl chloride in 30 ml of dichloromethane, 0.17 ml (2.5 mmol) of dimethyl sulfoxide was added dropwise at -78° C., followed by stirring for 5 minutes. To the solution, a solution of 0.303 g (0.820 mmol) of 4-(6,7-dihydro-4H-furo[3,2-c]pyridin-5-ylsulfonyl)phenylphenylmethanol in 10 ml of dichloromethane was added at -78° C., followed by stirring for 15 minutes. To this mixture, 0.69 ml (4.9 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=3/1) and washed with diethyl ether-hexane 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=3/1)
  7. washwashed with diethyl ether-hexane

Sources & evidence

ORD record
ord-e3dbe153951d4ea587bbaca1ee9dd350
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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