(1R,cis)2,2-dimethyl-3-(2,2,2-trichloroethoxycarbonylethynyl)-cyclopropane-carboxylic acid → (R)alpha-methyl-3-phenoxy-benzyl (IR,cis) 2,2-dimethyl-3-[3-oxo-3-(2,2,2-trichloroethoxy)-1-propynyl]-cyclopropane-carboxylate

HRID 569533Notes

Reaction equation

HRID 569533 reaction equation
[CH3:1][C:2]1([CH3:18])[C@@H:4]([C:5]#[C:6][C:7](=[O:14])[O:8][CH2:9][C:10]([Cl:13])([Cl:12])[Cl:11])[C@H:3]1[C:15]([OH:17])=[O:16].[O:19]([C:26]1[CH:27]=[C:28]([C@H:32](O)[CH3:33])[CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH3:1][C:2]1([CH3:18])[C@@H:4]([C:5]#[C:6][C:7](=[O:14])[O:8][CH2:9][C:10]([Cl:13])([Cl:11])[Cl:12])[C@H:3]1[C:15]([O:17][C@H:32]([CH3:33])[C:28]1[CH:29]=[CH:30][CH:31]=[C:26]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:27]=1)=[O:16]

Participants

3

Reactant 2

HCID 13093792(1R,cis)2,2-dimethyl-3-(2,2,2-trichloroethoxycarbonylethynyl)-cyclopropane-carboxylic acidHCID 22815813(1R)-1-(3-phenoxyphenyl)ethan-1-ol

Product 1

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

Procedure

Using the procedure of Step D of Example 9, 6 g of (1R,cis)2,2-dimethyl-3-[3-oxo-3-(2,2,2-trichloroethoxy)-1-propynyl]-cyclopropane-carboxylic acid and 4.1 g of 1-(R)(3-phenoxy-phenyl)-ethanol were reacted to obtain after chromatography and elution with an 8--2 mixture of cyclohexaneethyl acetate 4.38 g of (R)α-methoxy-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-[3-oxo-3-(2,2,2-trichloroethoxy)-1-propynyl]-cyclopropane-carboxylate.

Workup

  1. customwere reacted
  2. customto obtain
  3. washafter chromatography and elution
  4. additionwith an 8--2 mixture of cyclohexaneethyl acetate 4.38 g of (R)α-methoxy-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-[3-oxo-3-(2,2,2-trichloroethoxy)-1-propynyl]-cyclopropane-carboxylate

Sources & evidence

ORD record
ord-1e6d84310f8b446b9f7b898683ffe457
Source dataset
uspto-grants-1988_03
Patent number
US04732903

Reaction notes

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