Sodium borohydride → HCID 54071982, compound

HRID 1581099Notes

Reaction equation

HRID 1581099 reaction equation
[BH4-].[Na+].[CH3:3][CH:4]1[CH2:8][CH:7]([CH:9]=[CH:10][C:11](=[O:17])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])[C:5]1=[O:27]>[OH-].[Na+].C(O)C>[OH:27][CH:5]1[CH:4]([CH3:3])[CH2:8][CH:7]([CH:9]=[CH:10][CH:11]([OH:17])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:6]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 73796061HCID 73796061, compound

Product 1

HCID 54071982HCID 54071982, compoundYield 80.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent2×

Conditions

Temperature
10 °C

Procedure

A solution of sodium borohydride (0.18 g., 0.0046 mole) in 0.2N aqueous sodium hydroxide (1.8 ml.) was added dropwise to a solution of 7-[3-methyl-2-oxo-5-(3-oxo-1-octenyl)cyclopentyl]heptanoic acid (0.5 g., 0.0014 mole) in ethanol (15 ml.) and N aqueous sodium hydroxide (1.4 ml., 0.0014 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)-3-methylcyclopentyl]heptanoic acid (0.4 g., 80%) which required no further purification. N.M.R. (approximately 10% solution in deuterochloroform), 0.84 δ (triplet J=5c/s, terminal CH3), 0.95 δ (doublet J=6c/s, ring methyl), 1.31 δ (multiplet, chain CH2), 2.24 δ (triplet J=6c/s, CH2CO), 3.68 and 3.98 δ (overlapping multiplets, HCOH), 5.39 δ (multiplet CH=CH), 5.77 δ (singlet OH and COOH). (Found: C, 71.1; H, 10.7. C21H38O4 requires C, 71.2; H, 10.8%).

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-64a1b38c1c924d9f8d4ea831b828e35f
Source dataset
uspto-grants-1976_01
Patent number
US03935261

Reaction notes

Loading…