Acetic Acid → HCID 86734761, compound

HRID 2398202Notes

Reaction equation

HRID 2398202 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]/[CH:12]=[CH:13]\[CH2:14][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]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 9927744HCID 9927744, compound

Product 1

HCID 86734761HCID 86734761, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

50 mg of 7-[2-(3-hydroxy-3-pentyl-trans-1-propenyl)-5-oxo-cyclo-pentyl]-cis-5-heptenoic acid were dissolved in 20 ml of methanol and in the course of 1.5 hours three 50 mg portions of NaBH4 were added. The reaction solution was adjusted to pH 7 with glacial acetic acid, the solvent was distilled off under reduced pressure, the residue was acidified in 1 ml of H2O with 2 N hydrochloric acid to pH 1 and extracted three times with 150 ml portions of ether. The combined ether extracts were washed with water, dried and condensed.

Workup

  1. additionwere added
  2. distillationthe solvent was distilled off under reduced pressure
  3. extractionextracted three times with 150 ml portions of ether
  4. washThe combined ether extracts were washed with water
  5. customdried
  6. customcondensed

Sources & evidence

ORD record
ord-92494a7a52a24f129ad9929730442802
Source dataset
uspto-grants-1977_05
Patent number
US04024181

Reaction notes

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