Acetic Acid → (S)alpha-cyano-3-phenoxy-benzyl (IR,cis) 2,2-dimethyl-3-(2-carboxyethynyl)-cyclopropane-carboxylate

HRID 569523Notes

Reaction equation

HRID 569523 reaction equation
[CH3:1][C:2]1([CH3:34])[C@@H:4]([C:5]#[C:6][C:7]([O:9]CC(Cl)(Cl)Cl)=[O:8])[C@H:3]1[C:15]([O:17][C@H:18]([C:32]#[N:33])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:20]=1)=[O:16].C(O)(=O)C>[Zn].O>[CH3:1][C:2]1([CH3:34])[C@@H:4]([C:5]#[C:6][C:7]([OH:9])=[O:8])[C@H:3]1[C:15]([O:17][C@H:18]([C:32]#[N:33])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:20]=1)=[O:16]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 13093794(S)alpha-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-(2,2,2-trichloroethoxycarbonylethynyl)-cyclopropane-carboxylate

Product 1

HCID 13093796(S)alpha-cyano-3-phenoxy-benzyl (IR,cis) 2,2-dimethyl-3-(2-carboxyethynyl)-cyclopropane-carboxylateYield 96.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

5.9 g of zinc powder were introduced int a solution of 6.5 g of the product of Step D, 23.4 ml of acetic acid and 2.6 ml of water and the mixture was stirred for 1 hour and filtered. The filtrate was decanted and the organic phase was washed with water. The aqueous phase was extracted with methylene chloride and the combined organic phases were dried, filtered and evaporated to dryness to obtain 4.7 g of (S)α-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-(3-hydroxy-3-oxo-propynyl)-cyclopropane-carboxylate which was used as is for the next step.

Workup

  1. filtrationfiltered
  2. customThe filtrate was decanted
  3. washthe organic phase was washed with water
  4. extractionThe aqueous phase was extracted with methylene chloride
  5. customthe combined organic phases were dried
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-a1170d20e7114f5a9e9ab4294337e165
Source dataset
uspto-grants-1988_03
Patent number
US04732903

Reaction notes

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