Sodium Chloride → HCID 70615450, compound

HRID 2083796Notes

Reaction equation

HRID 2083796 reaction equation
C([O:3][C:4](=[O:27])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C@@H:11]1[C:15](=[CH:16][CH2:17][C:18]([OH:25])([CH3:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:14][CH2:13][C@H:12]1[OH:26])C.COCCOC.[OH-].[K+].[Na+].[Cl-]>C(OCC)C.O>[OH:26][C@@H:12]1[CH2:13][CH2:14][C:15](=[CH:16][CH2:17][C:18]([OH:25])([CH3:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C@H:11]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]([OH:27])=[O:3]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 80711,2-DimethoxyethaneHCID 14797Potassium HydroxideHCID 70615461HCID 70615461, compound

Product 1

HCID 70615450HCID 70615450, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 250 mg. 9β,15-dihydroxy-15-methyl-12-prostenoic acid ethyl ester (as mixture of the two 15-epimers), 20 ml. 1,2-dimethoxyethane, 0.3 g. KOH and 5 ml. water is stirred for 12 hours at room temperature, diluted with 40 ml. diethyl ether and saturated with NaCl. The organic phase is separated, washed twice with 15 ml. amounts of H2O and dried over MgSO4. Solvent is removed to obtain, as oily residue, 9β,15-dihydroxy-15-methyl-12-prostenoic acid as mixture of the 15-epimers.

Workup

  1. additionA mixture of 250 mg
  2. additiondiluted with 40 ml
  3. customThe organic phase is separated
  4. washwashed twice with 15 ml
  5. dry with materialamounts of H2O and dried over MgSO4
  6. customSolvent is removed

Sources & evidence

ORD record
ord-6d07b9cce5fd465ea42933190b116894
Source dataset
uspto-grants-1978_04
Patent number
US04086362

Reaction notes

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