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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1995159Generated: October 30, 2026

(2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile → (S)alpha-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[Z-2-(isopropoxycarbonyl)-ethenyl]-cyclopropane-carboxylate

https://huagongshe.com/reaction/1995159

Reaction equation

Participants

RoleNameHCIDCharge
Reactant(2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrileHCID 9837437—
Reactant(1R,cis) 2,2-dimethyl-3-[Z-2-(isopropoxycarbonyl)-ethenyl]-cyclopropane-carboxylic acidHCID 12807755—
Product(S)alpha-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[Z-2-(isopropoxycarbonyl)-ethenyl]-cyclopropane-carboxylateHCID 1310600669.6%

Reaction Steps

Using the procedure of Step D of Example 1, 900 mg of the product of Step C and 900 mg of (S)α-cyano-3-phenoxy-benzyl alcohol were reacted to obtain 1.8 g of raw product which was chromatographed over silica gel. Elution with a 9-1 cyclohexane-ethyl acetate mixture yielded 1.2 g of (S)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[Z-2-(isopropoxycarbonyl)-ethenyl]-cyclopropane-carboxylate with a specific rotation of [α]D20 =+54°±2° (c=0.4% in benzene).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04402972
Source datasetuspto-grants-1983_09
ORD IDord-b9ed0d28eb754d9885fce34dc523011a
Source noteuspto-grants-1983_09