HuagongsheHuagongshe Chemistry Print Report · For research reference only
(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
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile | HCID 9837437 | — |
| Reactant | (1R,cis) 2,2-dimethyl-3-[Z-2-(isopropoxycarbonyl)-ethenyl]-cyclopropane-carboxylic acid | HCID 12807755 | — |
| Product | (S)alpha-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[Z-2-(isopropoxycarbonyl)-ethenyl]-cyclopropane-carboxylate | HCID 13106006 | 69.6% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04402972 |
| Source dataset | uspto-grants-1983_09 |
| ORD ID | ord-b9ed0d28eb754d9885fce34dc523011a |
| Source note | uspto-grants-1983_09 |