Methanol → ACMC-20apjz

HRID 918113Notes

Reaction equation

HRID 918113 reaction equation
[OH:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16]C)=[O:15])=[CH:3]1.[OH-].[Na+].CO>O>[OH:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 3912664Norprostol

Product 1

HCID 3690897ACMC-20apjz

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.240 part of methyl 3-hydroxy-5-oxocyclopent-1-eneheptanoate, 10 parts by volume of 0.1 N sodium hydroxide and 7.9 parts of methanol is allowed to stand at room temperature for 16 hours, then diluted with water and extracted with ethyl acetate. The aqueous layer is acidified with 1 N hydrochloric acid and then extracted with ethyl acetate. The ethyl acetate extract is washed with water, dried over anhydrous sodium sulfate and stripped of solvent under reduced pressure. Chromatography of the crude product on silica gel with 50% ethyl acetate-benzene affords 3-hydroxy-5-oxocyclopent-1-eneheptanoic acid, melting at about 47°-48.5°. That compound is characterized further by absorption in the ultravoilet spectrum at about 222 millimicrons with a molecular extinction coefficient of about 7700 and a maximum in the nuclear magnetic resonance spectrum at about 87.2 ppm.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washis washed with water
  5. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-a23c3554cb314101b9a961be919a4759
Source dataset
uspto-grants-1976_07
Patent number
US03969391

Reaction notes

Loading…