Potassium thiocyanate → HCID 18594805, compound

HRID 1580232Notes

Reaction equation

HRID 1580232 reaction equation
CS(O[CH:6]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:7][CH2:8][C@@H:9]1[C@@H:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:12](=[O:25])[CH2:11][CH2:10]1)(=O)=O.[S-:31][C:32]#[N:33].[K+]>CN(C)C=O>[O:25]=[C:12]1[CH2:11][CH2:10][C@H:9]([CH2:8][CH2:7][CH:6]([S:31][C:32]#[N:33])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C@H:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

4

Reactant 2

HCID 516872Potassium thiocyanateHCID 18594876HCID 18594876, compound

Product 1

HCID 18594805HCID 18594805, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1 g. of ethyl 15-methanesulfonyloxy-9-oxo-prostanoate (Example 90) and 1 g. of dry potassium thiocyanate in 30 ml. of N,N-dimethylformamide is heated on the steam bath for 18 hours. The resulting mixture is poured into 150 ml. of water and extracted with ether. The extract is washed with water, dried with anhydrous magnesium sulfate and taken to dryness. Silica gel chromatography of the residue gives 462 mg. of oil; λmax. 4.67 (thiocyanate group) and 5.78 μ (carbonyl groups).

Workup

  1. additionThe resulting mixture is poured into 150 ml
  2. extractionof water and extracted with ether
  3. washThe extract is washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customSilica gel chromatography of the residue gives 462 mg

Sources & evidence

ORD record
ord-967e96d2725844f3a86cebb166b0d01d
Source dataset
uspto-grants-1976_01
Patent number
US03932472

Reaction notes

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