Acetic Acid → HCID 54059661, compound

HRID 2083792Notes

Reaction equation

HRID 2083792 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C@@H:11]1[C:15](=[CH:16][CH2:17][C:18](=[O:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:14][CH2:13][C@H:12]1[OH:25])[CH3:2].C(O)C.[BH4-].[Na+].C(O)(=O)C>O>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C@@H:11]1[C:15](=[CH:16][CH2:17][CH:18]([OH:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:14][CH2:13][C@H:12]1[OH:25])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 4311764Sodium borohydrideHCID 54372282HCID 54372282, compound

Product 1

HCID 54059661HCID 54059661, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2 g. 9β-hydroxy-15-oxo-12-prostenoic acid ethyl ester, dissolved in 20 ml. dry ethanol, is added with ice cooling under nitrogen with exclusion of moisture and stirring, portionwise over 15 minutes, 206 mg. NaBH4. The mixture is stirred 15 minutes more and 0.325 ml. glacial acetic acid is added dropwise thereto. The mixture is poured into 50 ml. of water. Solvent is removed by distillation and the residue is extracted three times with 15 ml. amounts of diethyl ether. The organic phase is washed with water and dried over Na2SO4. Solvent is removed to obtain as residue 9β,15-dihydroxy-12-prostenoic acid ethyl ester which, after chromatographic purification twice (first silica gel/dichloromethane:acetone = 10:1; then silica gel/petroleum ether:ethanol = 9:1), can be separated into the two 15-epimers:

Workup

  1. stirringThe mixture is stirred 15 minutes more
  2. additionThe mixture is poured into 50 ml
  3. customSolvent is removed by distillation
  4. extractionthe residue is extracted three times with 15 ml
  5. washThe organic phase is washed with water
  6. dry with materialdried over Na2SO4
  7. customSolvent is removed

Sources & evidence

ORD record
ord-06c29f493348460a862d0a0968a6e3f5
Source dataset
uspto-grants-1978_04
Patent number
US04086362

Reaction notes

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