Water → HCID 88745964, compound

HRID 1446893Notes

Reaction equation

HRID 1446893 reaction equation
CN(P(N(C)C)N(C)C)C.[C:11]([O:14][CH:15]([C:24](=[O:26])[CH3:25])[CH2:16][CH:17]1[C:19]([CH3:21])([CH3:20])[CH:18]1[CH:22]=O)(=[O:13])[CH3:12].[C:27](Cl)(Cl)([Cl:29])[Cl:28].O>C(OCC)C>[C:11]([O:14][CH:15]([C:24](=[O:26])[CH3:25])[CH2:16][C@H:17]1[C:19]([CH3:21])([CH3:20])[C@H:18]1[CH:22]=[C:27]([Cl:29])[Cl:28])(=[O:13])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 5943Carbon TetrachlorideHCID 15355Hexamethylphosphorous triamideHCID 20553527HCID 20553527, compound

Product 1

HCID 88745964HCID 88745964, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Tri(dimethylamino)phosphine (40 mmol) was added with stirring at -20° C. to a solution of 1-(2-formyl-3,3-dimethylcyclopropyl)-3-oxo-2-butyl acetate (14.2 mmol) and carbon tetrachloride (40 mmol) in diethyl ether (160 ml) kept under nitrogen. Then, the temperature of the mixture was allowed to rise to 20° C. Water (50 ml) was added, the mixture was stirred for 5 minutes and, after settling, the organic phase was isolated. The organic phase was washed with two 50-ml portions of water. The washed organic phase was dried over anhydrous magnesium sulphate and the solvent was evaporated from the dried solution to leave a residue (2.2 g) containing 1-[2-(2,2-dichlorovinyl)-3,3-dimethylcyclopropyl]-3-oxo-2-butyl acetate (100% (1R,cis), yield 54%).

Workup

  1. customto rise to 20° C
  2. customthe organic phase was isolated
  3. washThe organic phase was washed with two 50-ml portions of water
  4. dry with materialThe washed organic phase was dried over anhydrous magnesium sulphate
  5. customthe solvent was evaporated from the dried solution

Sources & evidence

ORD record
ord-b5c50bb1d6544f0d9ad78ce6c0eaf388
Source dataset
uspto-grants-1982_02
Patent number
US04314072

Reaction notes

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