Dimethyl Sulfoxide → HCID 57003203, compound

HRID 1886108Notes

Reaction equation

HRID 1886108 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[O:11]1[C@H:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)[C@H:12]1[CH2:13][OH:14].C(N(CC)CC)C>C(Cl)Cl>[O:11]1[C@H:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:23])([F:24])[F:25])[CH:17]=2)[C@H:12]1[CH:13]=[O:14]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 11769920HCID 11769920, compound

Product 1

HCID 57003203HCID 57003203, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 1.1 g of oxalyl chloride in 15 ml of methylene chloride is cooled to -65°-70° under argon and within a period of 2 minutes 1.5 g of dimethyl sulfoxide in 5 ml of methylene dichloride are added. After stirring for 10 minutes at -65°-70°, 1.7 g of (2R,3R)-2,3-epoxy-3-(3-trifluoromethylphenyl)-propanol in 15 ml of methylene chloride are added dropwise. After stirring for a further 30 minutes, 4 g of triethylamine are added dropwise, the temperature rising to -40°. The temperature is allowed to rise to 0° and the reaction mixture is poured onto phosphate buffer (pH 8). The organic phase is separated off and the aqueous phase is extracted with methylene chloride. The combined organic extracts are washed twice with brine, dried over sodium sulfate and concentrated by evaporation. Chromatography of the residue on silica gel with hexane/ethyl acetate (7:3) yields the title compound in the form of a colourless oil; IR (methylene chloride): 2820, 1730, 1330, 1165, 1125, 1070 cm-1. Rf =0.36 (hexane/ethyl acetate 3:2). [α]D20 (chloroform, 0.20%)=-17.5°±5°.

Workup

  1. additionare added
  2. stirringAfter stirring for a further 30 minutes
  3. customrising to -40°
  4. customto rise to 0°
  5. additionthe reaction mixture is poured onto phosphate buffer (pH 8)
  6. customThe organic phase is separated off
  7. extractionthe aqueous phase is extracted with methylene chloride
  8. washThe combined organic extracts are washed twice with brine
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-cc45662fd11a49259a0a082fe7683d1a
Source dataset
uspto-grants-1992_09
Patent number
US05149717

Reaction notes

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