HuagongsheHuagongshe Chemistry Print Report · For research reference only
Neopentyl alcohol → (S)alpha-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-[2-neopentyloxycarbonyl-ethynyl]-cyclopropane-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Neopentyl alcohol | HCID 6404 | — |
| Reactant | (S)alpha-cyano-3-phenoxy-benzyl (IR,cis) 2,2-dimethyl-3-(2-carboxyethynyl)-cyclopropane-carboxylate | HCID 13093796 | — |
| Product | (S)alpha-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-[2-neopentyloxycarbonyl-ethynyl]-cyclopropane-carboxylate | HCID 54365246 | 82.8% |
Reaction Steps
Using the procedure of Step A of Example 15, 3.89 g of (S)α-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-(2-carboxyethynyl)-cyclopropane-carboxylate and 1 g of neopentyl alcohol were reacted and the mixture was stirred at room temperature for 4 hours and was filtered. The filtrate was washed with N hydrochloric acid, with water, dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with an 8-2 cyclohexane-ethyl acetate mixture to obtain 3.8 g of (S)α-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-[2-neopentyloxycarbonyl-ethynyl]-cyclopropane-carboxylate melting at 67° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04547522 |
| Source dataset | uspto-grants-1985_10 |
| ORD ID | ord-507d9a70d097455db8cd57b3a6da2d34 |
| Source note | uspto-grants-1985_10 |