Sodium borohydride → 7-[2-Hydroxy-5-(3-hydroxy-1-octenyl)cyclopentyl]heptanoic acid

HRID 1581095Notes

Reaction equation

HRID 1581095 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][CH2:23][C:24]([OH:26])=[O:25]>[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][CH2:23][C:24]([OH:26])=[O:25]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 572983517-[2-Oxo-5-(3-oxo-1-octenyl)cyclopentyl]heptanoic acid

Product 1

HCID 533941777-[2-Hydroxy-5-(3-hydroxy-1-octenyl)cyclopentyl]heptanoic acidYield 58.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent2×

Conditions

Temperature
10 °C

Procedure

A solution of sodium borohydride (0.035 g., 0.0009 mole) in 0.2N aqueous sodium hydroxide (0.35 ml.) was added dropwise to a solution of 7-[2-oxo-5-(3-oxo-1-octenyl)cyclopentyl]heptanoic acid (0.14 g., 0.0004 mole) in ethanol (3 ml.) and N aqueous sodium hydroxide (0.42 ml., 0.0004 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 7-[2-hydroxy-5-(3-hydroxy-1-octenyl)cyclopentyl]heptanoic acid (0.08 g., 57%), νmax 1700 cm-1 and 980 cm-1 (liquid film), which required no further purification. N.M.R. (approximately 10% solution in deuterochloroform) 0.9 δ (triplet J=5c/s, terminal CH3), 1.1-2.0 δ (broad band, cyclic and chain CH2), 2.3 δ (triplet J=6c/s, CH2C=O) ~ 4.0 δ (broad mutiplet ##EQU5## 5.25 δ (broad singlet, OH), 5.4δ (broad peak ##EQU6##

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-6189fdf907814d5e91f8ba558a0852bc
Source dataset
uspto-grants-1976_01
Patent number
US03935261

Reaction notes

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