Potassium Carbonate → HCID 18594687, compound

HRID 2071347Notes

Reaction equation

HRID 2071347 reaction equation
C([O:4][C@@H:5]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:6][CH2:7][C@@H:8]1[C@@H:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:11](=[O:23])[CH2:10][CH2:9]1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>>[OH:4][C@@H:5]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:6][CH2:7][C@@H:8]1[C@@H:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:11](=[O:23])[CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 11430Potassium CarbonateHCID 18594686HCID 18594686, compound

Product 1

HCID 18594687HCID 18594687, compound

Procedure

A solution of 2.26 g. of methyl 15(S)-acetoxy-9-oxo-prostanoate (Example 15) in 300 ml. of absolute alcohol containing 790 mg. of potassium carbonate is stirred at ambient temperature for 72 hours then concentrated to near dryness under reduced pressure. The resulting mixture is extracted with ether. The combined extracts are washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate and taken to dryness to give 1.83 g. of an oil. Purification by silica gel chromatography affords the subject compound as an oil; λ max. 2.92 (hydroxyl group), 5.74 μ (carbonyl groups); [α]D25 -23° C. (0.2% in CHCL3).

Workup

  1. concentrationthen concentrated
  2. extractionThe resulting mixture is extracted with ether
  3. washThe combined extracts are washed with saturated sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customto give 1.83 g
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-0ffe5f0cd3c54c858abaf26fd496fb38
Source dataset
uspto-grants-1977_09
Patent number
US04046787

Reaction notes

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