HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium borohydride → (1S,5R,6R,7R)-6-[(E)-(3S,4RS)-3-hydroxy-4-methyl-1-nonene-6-ynyl]-7-benzoyloxy-2-oxabicyclo[3.3.0]octane-3-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | (1S,5R,6R,7R)-7-Benzoyloxy-6-[(E)-(4RS)-4-methyl-3-oxonon-1-en-6-inyl]-2-oxabicyclo[3,3,0]octan-3-one | HCID 13472481 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | (1S,5R,6R,7R)-6-[(E)-(3S,4RS)-3-hydroxy-4-methyl-1-nonene-6-ynyl]-7-benzoyloxy-2-oxabicyclo[3.3.0]octane-3-one | HCID 13472483 | — |
Reaction Conditions
| Temperature | -40 °C |
|---|
Reaction Steps
3.4 of sodium borohydride is added batchwise to a solution of 6 g of the ketone prepared in example (6e) in 200 ml of methanol, at -40° C., and the mixture is stirred for 1 h at -40° C. under argon. Next it is diluted with ether, washed with water until neutral, dried over magnesium sulfate and vacuum evaporated. By means of column chromatography on silcia gel using ether/hexane (8/2), first 2.6 g of the title compound (3-alpha-hydroxy) is elutriated, next, as the more polar component, 1.9 g of the corresponding isomeric 3 beta-hydroxy compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04364950 |
| Source dataset | uspto-grants-1982_12 |
| ORD ID | ord-7e49187b9e884bf9a1ba2d694c18f670 |
| Source note | uspto-grants-1982_12 |