HuagongsheHuagongshe Chemistry Print Report · For research reference only
Bis(trimethylsilyl)acetylene → HCID 14261110, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Bis(trimethylsilyl)acetylene | HCID 84564 | — |
| Reactant | Cyclohexylacetyl chloride | HCID 2757989 | — |
| Reactant | 1-Cyclohexyl-3-butyn-2-one | HCID 14261108 | — |
| Reactant | HCID 67416678 | HCID 67416678 | — |
| Product | HCID 14261110 | HCID 14261110 | — |
Reaction Steps
As directed by D. R. M. Walton and F. Waugh, J. Organomet. Chem. 37, 45 (1972), bis(trimethylsilyl)acetylene is acylated with cyclohexylacetic acid chloride and hydrolysed with aqueous/methanolic borax solution to 1-cyclohexyl-3-butyn-2-one. Reduction with (S)-B-(3-pinanyl)-9-borabicyclo[3.3.1]nonane ((S)-Alpine-Borane®, Aldrich, 88% ee) as directed by M. M Midland et al., Tetrahedron 40, 1371 (1984) yields 1-cyclohexyl-3-butyn-2(S)-ol.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04898977 |
| Source dataset | uspto-grants-1990_02 |
| ORD ID | ord-ac2f05701fc6453b8e6d84bf1668439a |
| Source note | uspto-grants-1990_02 |