HCID 70589709, compound → HCID 70588333, compound

HRID 225376Notes

Reaction equation

HRID 225376 reaction equation
[CH3:1][C:2]([O:25]C1CCCCO1)([CH2:20][CH2:21][C:22]#[C:23][CH3:24])/[CH:3]=[CH:4]/[C@@H:5]1[C@@H:9]([CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:8](=[O:19])[CH2:7][CH2:6]1>C(O)(=O)C.O.C1COCC1>[OH:25][C:2]([CH3:1])([CH2:20][CH2:21][C:22]#[C:23][CH3:24])/[CH:3]=[CH:4]/[C@@H:5]1[C@@H:9]([CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:8](=[O:19])[CH2:7][CH2:6]1

Participants

3

Reactant 1

HCID 70589709HCID 70589709, compound

Product 1

HCID 70588333HCID 70588333, compound

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

300 mg. of (5Z,13E)-(15RS)-15-methyl-9-oxo-15-(tetrahydropyran-2-yloxy)-5,13-prostadien-18-ynoic acid is agitated for 16 hours at room temperature with 8 ml. of a mixture of glacial acetic acid/water/THF (65/35/10); the mixture is then evaporated under vacuum, and the residue is purified by chromatography on silica gel. With methylene chloride/5% methanol, 205 mg. of the title compound is obtained as a colorless oil.

Workup

  1. customthe mixture is then evaporated under vacuum
  2. customthe residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a477b7bc0a364b458cb803a60b74f549
Source dataset
uspto-grants-1980_11
Patent number
US04235930

Reaction notes

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