Dimethyl Sulfoxide → HCID 54438747, compound

HRID 442991Notes

Reaction equation

HRID 442991 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([O:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23]([CH3:26])(=[O:25])=[O:24])(=[O:16])=[O:15])[CH:5]=[C:6]([CH:12]=1)[O:7][CH2:8][CH2:9][CH2:10][OH:11].CS(C)=O.C(N(CC)C(C)C)(C)C>ClCCl>[CH3:1][C:2]1[CH:3]=[C:4]([O:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23]([CH3:26])(=[O:24])=[O:25])(=[O:15])=[O:16])[CH:5]=[C:6]([CH:12]=1)[O:7][CH2:8][CH2:9][CH:10]=[O:11]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 22722527HCID 22722527, compound

Product 1

HCID 54438747HCID 54438747, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-[5-methyl-3-[2-(methylsulfonyl)phenylsulfonyloxy]-phenoxy]propanol (1.16 g, 2.9 mmol), as prepared in the preceding step, anhydrous dimethyl sulfoxide (0.62 mL, 8.7 mmol), and N,N-diisopropylethylamine (1.0 mL, 6.1 mmol) in anhydrous dichloromethane (30 mL) was treated with sulfur trioxide pyridine complex (0.97 g 6.1 mmol) at 0° C. The reaction mixture was stirred for 0.75 h before quenching with 10% aqueous citric acid (40 mL). The dichloromethane layer was separated and the aqueous layer was extracted with dichloromethane (4×40 mL). The dichloromethane layers were combined and washed with brine, dried, and evaporated to dryness. The material was used without purification in the next step.

Workup

  1. additionwas treated with sulfur trioxide pyridine complex (0.97 g 6.1 mmol) at 0° C
  2. custombefore quenching with 10% aqueous citric acid (40 mL)
  3. customThe dichloromethane layer was separated
  4. extractionthe aqueous layer was extracted with dichloromethane (4×40 mL)
  5. washwashed with brine
  6. customdried
  7. customevaporated to dryness
  8. customThe material was used without purification in the next step

Sources & evidence

ORD record
ord-1aefca373f914798ac2862632f43b030
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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