Thionyl Chloride → HCID 67768649, compound

HRID 260722Notes

Reaction equation

HRID 260722 reaction equation
S(Cl)(Cl)=O.[CH3:5][C:6](O)([C:17]([F:20])([F:19])[F:18])[CH2:7][CH:8]1[CH:10]([C:11]([O:13][CH3:14])=[O:12])[C:9]1([CH3:16])[CH3:15]>O>[CH3:15][C:9]1([CH3:16])[CH:8](/[CH:7]=[C:6](\[CH3:5])/[C:17]([F:18])([F:19])[F:20])[CH:10]1[C:11]([O:13][CH3:14])=[O:12]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22400572HCID 22400572, compound

Product 1

HCID 67768649HCID 67768649, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

160 ml of thionyl chloride were added at 0° C. to 80.5 g of methyl 2,2-dimethyl-3-(2-methyl-2-hydroxy-3,3,3-trifluoropropylcyclopropane carboxylate of Stage C. The mixture was refluxed for 48 hours, cooled, poured into ice-cooled water and extracted with isopropyl ether. The organic phases were washed with water and after drying over magnesium sulfate and evaporation to dryness, the crude product was chromatographed on silica with a hexane-AcOEt mixture (9-1), then rechromatographed with a hexane--acetone mixture (99-1) to obtain 22.02 g of the starting alcohol, 11.71 g of the exo+Z isomer mixture and 23.31 g of the expected product.

Workup

  1. temperatureThe mixture was refluxed for 48 hours
  2. temperaturecooled
  3. additionpoured into ice-
  4. extractionextracted with isopropyl ether
  5. washThe organic phases were washed with water
  6. dry with materialafter drying over magnesium sulfate and evaporation to dryness
  7. customthe crude product was chromatographed on silica with a hexane-AcOEt mixture (9-1)
  8. customrechromatographed with a hexane

Sources & evidence

ORD record
ord-316bf7f4f05641549bc1466642f8aa68
Source dataset
uspto-grants-1996_06
Patent number
US05530022

Reaction notes

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