Hydrochloric Acid → HCID 18594825, compound

HRID 1580239Notes

Reaction equation

HRID 1580239 reaction equation
[OH:1][C@@H:2]1[CH2:17][CH2:16][C@H:15]([CH2:18][CH2:19][CH:20]([OH:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C@H:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12]CC)=[O:11].[OH-].[K+].Cl>CO.O>[OH:1][C@@H:2]1[CH2:17][CH2:16][C@H:15]([CH2:18][CH2:19][CH:20]([OH:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C@H:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 18594900HCID 18594900, compound

Product 1

HCID 18594825HCID 18594825, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of ethyl 9β,15-dihydroxyprostanoate in 32 ml. of methanol-water (1:1), containing 890 mg. of potassium hydroxide is kept at ambient temperature for 18 hours. The solution is acidified with dilute hydrochloric acid and extracted several times with ether. The ether phase is washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate and taken to dryness to give 1.63 g. of an oil; nmr 3H singlet δ 5.53 (hydroxyl and carboxyl protons), 1H singlet 4.23 (9β-carbinolic proton, 30%), 1H singlet 3.90 (9α-carbinolic proton, 70%), 1H singlet 3.65 (15-carbinolic proton), and 3H distorted triplet 0.90 (terminal methyl).

Workup

  1. extractionextracted several times with ether
  2. washThe ether phase is washed with saturated sodium chloride solution
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customto give 1.63 g

Sources & evidence

ORD record
ord-b102e425bdcf41d3897a6cd0ab24d964
Source dataset
uspto-grants-1976_01
Patent number
US03932472

Reaction notes

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