Acetic Acid → 11-Oxo-15,20-cycloprosta-8(12),13,15,17,19-pentaen-1-oic acid

HRID 1576412Notes

Reaction equation

HRID 1576412 reaction equation
[OH:1][CH:2]1[CH2:6][C:5](=O)[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[C:3]1[CH:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C.[BH4-].[Na+].C(O)(=O)C>C(O)C.O>[O:1]=[C:2]1[CH2:6][CH2:5][C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[C:3]1[CH:17]=[CH:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 681356993-Hydroxy-5-oxo-2-styrylcyclopent-1-eneheptanoic acid

Product 1

HCID 6814696211-Oxo-15,20-cycloprosta-8(12),13,15,17,19-pentaen-1-oic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

6 Parts of 3-hydroxy-5-oxo-2-styrylcyclopent-1-eneheptanoic acid is dissolved in 71 parts of ethanol and cooled to about 10° as 1.88 parts of triethylamine is added. The solution is stirred as 1.5 parts of sodium borohydride dissolved in 100 parts of water is added dropwise at 10°-15°. After stirring at about 15° for 4 hours, the mixture is acidified with dilute aqueous acetic acid and the oily precipitate is extracted with ethyl acetate. The organic solution is washed with dilute aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated to an orange oil. Then the oil is taken up in benzene and chromatographed on silicic acid as the column is eluted with benzene containing increasing amounts of ethyl acetate. A fraction eluted with 30% ethyl acetate is crystallized from ethyl acetate-hexane to give pale yellow crystals of 3-oxo-2-styrylcyclopent-1-eneheptanoic acid, melting at about 118°-120°. That compound displays, in chloroform, absorption peaks in the infrared spectrum at about 2940 and 1700 reciprocal centimeters and an absorption band, in methanol, in the ultraviolet spectrum at about 288 millimicrons with a molecular extinction coefficient of about 24,400. That compound is represented by the following structural formula ##SPC18##

Workup

  1. additionis added
  2. additionis added dropwise at 10°-15°
  3. extractionthe oily precipitate is extracted with ethyl acetate
  4. washThe organic solution is washed with dilute aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated to an orange oil
  7. customchromatographed on silicic acid as the column
  8. washis eluted with benzene containing
  9. temperatureincreasing amounts of ethyl acetate
  10. washA fraction eluted with 30% ethyl acetate
  11. customis crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-34eb4850a65c40bf870f32a6ae71d2c7
Source dataset
uspto-grants-1976_09
Patent number
US03980700

Reaction notes

Loading…