Water → HCID 86747863, compound

HRID 1033962Notes

Reaction equation

HRID 1033962 reaction equation
[C:1](=[O:4])([O-:3])[O-].[K+].[K+].[CH3:7][C:8]1([CH3:21])[C@@H:10]([CH:11](Br)[C:12](=O)CBr)[C@H:9]1[C:17]([O:19][CH3:20])=[O:18].O>O1CCCC1>[CH3:7][C:8]1([CH3:21])[C@@H:10](/[CH:11]=[CH:12]\[C:1]([OH:3])=[O:4])[C@H:9]1[C:17]([O:19][CH3:20])=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 10936779HCID 10936779, compound

Product 1

HCID 86747863HCID 86747863, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 ml of a 1N solution of potassium carbonate was placed under an inert gas atmosphere and then a solution of 0.342 g of methyl (1R,cis) 2,2-dimethyl-3-(1,3-dibromo-2-oxopropyl)-cyclopropane-1-carboxylate in 1.5 ml of tetrahydrofuran was added at about +5° C. The mixture was stirred for 90 minutes and then the temperature was allowed to rise to 20° C. and stirring was continued for 4 hours. Water was added and extraction was carried out with methylene chloride. The organic phase was dried and the solvent was evaporated. The residue was chromatographed on silica, eluting with a methylene chloride - ethanol mixture (97-3) to obtain 0.046 g of the expected product.

Workup

  1. customto rise to 20° C.
  2. stirringstirring
  3. waitwas continued for 4 hours
  4. extractionextraction
  5. customThe organic phase was dried
  6. customthe solvent was evaporated
  7. customThe residue was chromatographed on silica
  8. washeluting with a methylene chloride - ethanol mixture (97-3)

Sources & evidence

ORD record
ord-c4d7ba1ae46e4cd9941ed84d76c8ac94
Source dataset
uspto-grants-1994_05
Patent number
US05312964

Reaction notes

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