Acetic Acid → 7-[2-(3-Hydroxy-3-pentyl-trans-1-propenyl)-5-hydroxy-cyclopentyl]-cis-4-heptenoic acid

HRID 46709Notes

Reaction equation

HRID 46709 reaction equation
[OH:1][CH:2]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])/[CH:3]=[CH:4]/[CH:5]1[CH2:9][CH2:8][C:7](=[O:10])[CH:6]1[CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][C:17]([OH:19])=[O:18].[BH4-].[Na+].C(O)(=O)C>CO>[OH:1][CH:2]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])/[CH:3]=[CH:4]/[CH:5]1[CH2:9][CH2:8][CH:7]([OH:10])[CH:6]1[CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][C:17]([OH:19])=[O:18]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 867358317-[2-(3-Hydroxy-3-pentyl-trans-1-propenyl)-5-oxocyclopentyl]-cis-4-heptenoic acid

Product 1

HCID 867358307-[2-(3-Hydroxy-3-pentyl-trans-1-propenyl)-5-hydroxy-cyclopentyl]-cis-4-heptenoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

150 mg of 7-[2-(3-hydroxy-3-pentyl-trans-1-propenyl)-5-oxocyclopentyl]-cis-4-heptenoic acid were dissolved in 20 ml of methanol and three times each time 150 mg of NaBH4 were added within the course 11/2 hours. The reaction solution was adjusted to pH 7 by means of glacial acetic acid, the solvent was removed by distillation under reduced pressure, the residue was acidified with 2N-HCl to pH 1 and extracted thrice with 150 ml of ether. After washing, the organic phase was concentrated.

Workup

  1. customthe solvent was removed by distillation under reduced pressure
  2. extractionextracted thrice with 150 ml of ether
  3. washAfter washing
  4. concentrationthe organic phase was concentrated

Sources & evidence

ORD record
ord-dc88e9eb07ef4e82890e6b61f58b1a11
Source dataset
uspto-grants-1979_11
Patent number
US04174458

Reaction notes

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