Sodium borohydride → 6-[2-Hydroxy-5-(3-hydroxy-1-octenyl)cyclopentyl]-hexanoic acid

HRID 1581105Notes

Reaction equation

HRID 1581105 reaction equation
[BH4-].[Na+].[O:3]=[C:4]1[CH2:8][CH2:7][CH:6]([CH:9]=[CH:10][C:11](=[O:17])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:5]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24]>[OH-].[Na+].C(O)C>[OH:3][CH:4]1[CH2:8][CH2:7][CH:6]([CH:9]=[CH:10][CH:11]([OH:17])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:5]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 681198936-[2-Oxo-5-(3-oxo-1-octenyl)cyclopentyl]hexanoic acid

Product 1

HCID 541990176-[2-Hydroxy-5-(3-hydroxy-1-octenyl)cyclopentyl]-hexanoic acidYield 86%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent2×

Conditions

Temperature
10 °C

Procedure

A solution of sodium borohydride (0.2 g., 0.005 mole) in 0.2N aqueous sodium hydroxide (2 ml.) was added dropwise to a solution of 6-[2-oxo-5-(3-oxo-1-octenyl)cyclopentyl]hexanoic acid (0.61 g., 0.0019 mole) in ethanol (15 ml.) and N aqueous sodium hydroxide (1.9 ml., 0.0019 mole). 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 and evaporated to give 6-[2-hydroxy-5-(3-hydroxy-1-octenyl)cyclopentyl]-hexanoic acid (0.53 g., 86%) which required no further purification. N.M.R. (approximately 10% solution in deuterochloroform) 0.82 δ (triplet J=51/2c/s, terminal CH3), 1.32 δ (multiplet, chain CH2), 1.63 δ (multiplet CH--C=C), 2.30 δ (triplet J=61/2c/s, CH2CO), 3.6-4.3 δ (overlapping multiplets, HCOH), 4.90 δ (singlet OH and COOH), 5.41 δ (multiplet, CH=CH). (Found: C, 69.7: H, 10.5. C19H34O4 requires C, 69.9; H, 10.5%).

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

Sources & evidence

ORD record
ord-944f74f18b55401e915e87ab3e58e716
Source dataset
uspto-grants-1976_01
Patent number
US03935261

Reaction notes

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