(2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile → HCID 86739824, compound

HRID 1154417Notes

Reaction equation

HRID 1154417 reaction equation
[CH3:1][C:2]1([CH3:16])[C@@H:4](/[CH:5]=[C:6](/[Br:12])\[C:7](=[O:11])[O:8][CH2:9][CH3:10])[C@H:3]1[C:13]([OH:15])=[O:14].[C:17]([C@@H:19](O)[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:21]=1)#[N:18]>C(Cl)(Cl)Cl>[CH3:16][C:2]1([CH3:1])[C@@H:4](/[CH:5]=[C:6](/[Br:12])\[C:7](=[O:11])[O:8][CH2:9][CH3:10])[C@H:3]1[C:13]([O:15][C@H:19]([C:17]#[N:18])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:21]=1)=[O:14]

Participants

4

Reactant 2

HCID 9837437(2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrileHCID 86739825HCID 86739825, compound

Product 1

HCID 86739824HCID 86739824, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Using the procedure of Example 1, the product of Step A and (S)α-cyano-3-phenoxy-benzyl alcohol were reacted to obtain (S)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3(E)-[2-bromo-3-oxo-3-ethoxy-propenyl]-cyclopropane-carboxylate with a specific rotation of [α]D20 =-70.5°±2° (c=0.7% in chloroform).

Sources & evidence

ORD record
ord-cab57c8646cc4a8b842fc0e16ae43b0a
Source dataset
uspto-grants-1984_12
Patent number
US04489093

Reaction notes

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