Sodium borohydride → 7-[2-Hydroxy-5-(4-ethyl-3-hydroxyoct-1-enyl)-cyclopentyl]heptanoic acid

HRID 1581110Notes

Reaction equation

HRID 1581110 reaction equation
[BH4-].[Na+].[O:3]=[C:4]1[CH2:8][CH2:7][CH:6]([CH:9]=[CH:10][C:11](=[O:19])[CH:12]([CH2:17][CH3:18])[CH2:13][CH2:14][CH2:15][CH3:16])[CH:5]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27]>[OH-].[Na+].C(O)C>[OH:3][CH:4]1[CH2:8][CH2:7][CH:6]([CH:9]=[CH:10][CH:11]([OH:19])[CH:12]([CH2:17][CH3:18])[CH2:13][CH2:14][CH2:15][CH3:16])[CH:5]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 737960607-[2-Oxo-5-(4-ethyl-3-oxo-1-octenyl)cyclopentyl]heptanoic acid

Product 1

HCID 545023717-[2-Hydroxy-5-(4-ethyl-3-hydroxyoct-1-enyl)-cyclopentyl]heptanoic acidYield 14.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent2×

Conditions

Temperature
10 °C

Procedure

A solution of sodium borohydride (0.095 g.) in 0.2N aqueous sodium hydroxide (0.95 ml.) was added dropwise to a solution of 7-[2-oxo-5-(4-ethyl-3-oxo-1-octenyl)cyclopentyl]heptanoic acid (0.4 g.) in ethanol (9 ml.) and N aqueous sodium hydroxide (1.2 ml.). The resulting solution was stirred for 1 day, and then the ethanol was removed in vacuo. A small quantity of water was added, and the solution was extracted twice with diethyl ether (to remove non-acidic material). The aqueous solution was covered with a layer of diethyl ether and acidified to pH 1 by the dropwise addition of concentrated hydrochloric acid, cooling the solution to about 10°C. The ether layer was separated and the aqueous layer extracted twice more with diethyl ether. The combined ether extracts were dried over magnesium sulphate, evaporated and purified by preparative thin-layer chromatography to give 7[2-hydroxy-5-(4-ethyl-3-hydroxy-1-octenyl)cyclopentyl]heptanoic acid (60 mg.), νmax 1700cm-1, 980 cm- 1. (Found: C, 71.0; H, 10.4. C22H40O4 requires C, 71.7; H, 10.9%).

Workup

  1. customthe ethanol was removed in vacuo
  2. additionA small quantity of water was added
  3. extractionthe solution was extracted twice with diethyl ether (to remove non-acidic material)
  4. additionacidified to pH 1 by the dropwise addition of concentrated hydrochloric acid
  5. customThe ether layer was separated
  6. extractionthe aqueous layer extracted twice more with diethyl ether
  7. dry with materialThe combined ether extracts were dried over magnesium sulphate
  8. customevaporated
  9. custompurified by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-72800705c8964953adeb73ce860b0aa3
Source dataset
uspto-grants-1976_01
Patent number
US03935261

Reaction notes

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