(S)alpha-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-[2-(1,1-dimethylallyloxycarbonyl)-ethynyl]-cyclopropane-carboxylate → (S)alpha-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-[Z-2-(1,1-dimethylallyloxycarbonyl)-ethenyl]-cyclopropane-carboxylate

HRID 464470Notes

Reaction equation

HRID 464470 reaction equation
[CH3:1][C:2]1([CH3:34])[C@@H:4]([C:5]#[C:6][C:7]([O:9][C:10]([CH3:14])([CH3:13])[CH:11]=[CH2:12])=[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]>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:34])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:9][C:10]([CH3:13])([CH3:14])[CH:11]=[CH2:12])=[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

3

Reactant 1

HCID 86739012(S)alpha-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-[2-(1,1-dimethylallyloxycarbonyl)-ethynyl]-cyclopropane-carboxylate

Product 1

HCID 86739013(S)alpha-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-[Z-2-(1,1-dimethylallyloxycarbonyl)-ethenyl]-cyclopropane-carboxylateYield 81.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Using the procedure of Step B of Example 15, 450 mg of the product of Step A were reacted to obtain 370 mg of (S)α-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-[Z-2-(1,1-dimethylallyloxycarbonyl)-ethenyl]-cyclopropane-carboxylate with a specific rotation of [α]D20 =+40° (c=0.5% in benzene).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-8cf1211e805a4685a9d7e896eedaa7e4
Source dataset
uspto-grants-1985_10
Patent number
US04547522

Reaction notes

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