HuagongsheHuagongshe Chemistry Print Report · For research reference only
(5Z,13E)-(11R,15RS)-15-methyl-9-oxo-11,15-bis(tetrahydropyran-2-yloxy)-5,13-prostadien-18-ynoic acid → (5Z,13E)-(11R,15RS)-11,15-Dihydroxy-15-methyl-9-oxo-5,13-prostadien-18-ynoic Acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (5Z,13E)-(11R,15RS)-15-methyl-9-oxo-11,15-bis(tetrahydropyran-2-yloxy)-5,13-prostadien-18-ynoic acid | HCID 70588225 | — |
| Solvent | AcOH THF water | HCID 21877175 | — |
| Product | (5Z,13E)-(11R,15RS)-11,15-Dihydroxy-15-methyl-9-oxo-5,13-prostadien-18-ynoic Acid | HCID 70588404 | — |
Reaction Steps
500 mg. of (5Z,13E)-(11R,15RS)-15-methyl-9-oxo-11,15-bis(tetrahydropyran-2-yloxy)-5,13-prostadien-18-ynoic acid is agitated for 16 hours at 20° with 15 ml. of a mixture of glacial acetic acid/water/THF (65/35/10), then evaporated under vacuum, and the remainder purified by column chromatography on silica gel. With methylene chloride/5% methanol, 260 mg. of the title compound is obtained in the form of an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04235930 |
| Source dataset | uspto-grants-1980_11 |
| ORD ID | ord-d39a4619f5154c63a8c4d6b984057669 |
| Source note | uspto-grants-1980_11 |