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Acetic Acid → (R)alpha-methyl-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-[3-oxo-3-hydroxy-1-propynyl]-cyclopropane-carboxylate

HRID 1639447
Notes
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Reaction equation

HRID 1639447 reaction equation
[CH3:1][C:2]1([CH3:33])[C@@H:4]([C:5]#[C:6][C:7](=[O:14])[O:8]CC(Cl)(Cl)Cl)[C@H:3]1[C:15]([O:17][C@H:18]([CH3:32])[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.O>C(Cl)Cl.[Zn]>[CH3:1][C:2]1([CH3:33])[C@@H:4]([C:5]#[C:6][C:7](=[O:8])[OH:14])[C@H:3]1[C:15]([O:17][C@H:18]([CH3:32])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:20]=1)=[O:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 53655047(R)alpha-methyl-3-phenoxy-benzyl (IR,cis) 2,2-dimethyl-3-[3-oxo-3-(2,2,2-trichloroethoxy)-1-propynyl]-cyclopropane-carboxylate

Product 1

HCID 54097883(R)alpha-methyl-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-[3-oxo-3-hydroxy-1-propynyl]-cyclopropane-carboxylateYield 98.8%

Reagents, catalysts & solvents 2

HCID 23994
Zinc
Catalyst
2×
HCID 6344DichloromethaneSolvent

Procedure

A solution of 4.16 g of the product of Step A in 4 ml of methylene chloride was admixed with 45 ml of acetic acid containing 10% of water and 0.53 g of zinc powder and the mixture was stirred for 30 minutes at room temperature, then another 0.53 g of zinc powder were added 4 times until The reaction was complete and after 3 hours contact, the mixture was filtered. The filtrate was extracted with methylene chloride and the organic phase was washed with water, dried and evaporated to dryness by azeotropic distillation with toluene to obtain 3.05 g of (R)α-methyl-3-phenoxy-benzyl (IR,cis) 2,2-dimethyl-3-[3-oxo-3-hydroxy-1-propynyl]-cyclopropane-carboxylate.

Workup

  1. waitwas complete and after 3 hours
  2. filtrationcontact, the mixture was filtered
  3. extractionThe filtrate was extracted with methylene chloride
  4. washthe organic phase was washed with water
  5. customdried
  6. customevaporated to dryness by azeotropic distillation with toluene

Sources & evidence

ORD record
ord-5ad33230344e4f0489b09b2bcdc9f27e
Source dataset
uspto-grants-1989_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04883806

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes