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

HRID 1639446Notes

Reaction equation

HRID 1639446 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].CC1(C)[C@@H](/C=C\C(=O)OCCOC)[C@H]1C(O[C@H:35]([CH3:49])[C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([O:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:37]=1)=O.O(C1C=C(C(O)C)C=CC=1)C1C=CC=CC=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:35]([CH3:49])[C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([O:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:37]=1)=[O:16]

Participants

4

Reactant 3

HCID 128824191-(3-Phenoxyphenyl)ethanolHCID 13093792(1R,cis)2,2-dimethyl-3-(2,2,2-trichloroethoxycarbonylethynyl)-cyclopropane-carboxylic acidHCID 70489338(R)alpha-methyl-3-phenoxy-benzyl (IR,cis) 2,2-dimethyl-3-[(Z) 3-oxo-3-(2-methoxyethoxy)-1-propenyl]-cyclopropane-carboxylate

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 (IR,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 cyclohexane-ethyl acetate 4.38 g of (R)α-methoxy-3-phenoxy-benzyl (IR, 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 cyclohexane-ethyl acetate 4.38 g of (R)α-methoxy-3-phenoxy-benzyl (IR, cis) 2,2-dimethyl-3-[3-oxo-3-(2,2,2-trichloroethoxy)-1-propynyl]-cyclopropane-carboxylate

Sources & evidence

ORD record
ord-775bca46d1234b2fb3fce41f78a61083
Source dataset
uspto-grants-1989_11
Patent number
US04883806

Reaction notes

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