(2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile → HCID 86739818, compound

HRID 1383204Notes

Reaction equation

HRID 1383204 reaction equation
[CH3:1][C:2]1([CH3:15])[C@@H:4](/[CH:5]=[C:6](\[Br:11])/[C:7](=[O:10])[O:8][CH3:9])[C@H:3]1[C:12]([OH:14])=[O:13].[C:16]([C@@H:18](O)[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)#[N:17]>C(Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:15])[C@@H:4](/[CH:5]=[C:6](\[Br:11])/[C:7](=[O:10])[O:8][CH3:9])[C@H:3]1[C:12]([O:14][C@H:18]([C:16]#[N:17])[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:13]

Participants

4

Reactant 2

HCID 9837437(2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrileHCID 86739816HCID 86739816, compound

Product 1

HCID 86739818HCID 86739818, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Using the procedure of Example 1, the product of Step C and (S)α-cyano-3-phenoxy-benzyl alcohol were reacted to obtain (S)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3(Z)-[2-bromo-3-oxo-3-methoxy-propenyl]-cyclopropane-1-carboxylate with a specific rotation of [α]D20 =+29.5°±2.5° (c=0.5% in chloroform).

Sources & evidence

ORD record
ord-cebbd585de1e447eb3d4ba3eda724ea5
Source dataset
uspto-grants-1989_02
Patent number
US04808749

Reaction notes

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