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

HRID 464453Notes

Reaction equation

HRID 464453 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 powdered zinc were added to a solution of 6.5 g of the product of Step C, 23.4 ml of acetic acid and 2.6 ml of water and the mixture was stirred for one hour and was filtered. The filtrate was decanted and the organic phase was washed with water. The combined aqueous phases were extracted with methylene chloride and the combined organic phases were dried, filtered and evaporated to dryness to obtain 4.7 g of crude (S)α-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-(2-carboxyethynyl)-cyclopropane-carboxylate used as is for the next step.

Workup

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

Sources & evidence

ORD record
ord-2aac0abb4b6942658a36ab3217501d96
Source dataset
uspto-grants-1985_10
Patent number
US04547522

Reaction notes

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