Dimethylformamide → HCID 18594803, compound

HRID 2071340Notes

Reaction equation

HRID 2071340 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.CN(C)C=O.[Cl-:36].[Li+]>O>[Cl:36][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

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 433294Lithium ChlorideHCID 18594876HCID 18594876, compound

Product 1

HCID 18594803HCID 18594803, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.35 g. of ethyl 15-methanesulfonyloxy 9-oxo-prostanoate (Example 90) in 40 ml. of N,N-dimethylformamide containing 650 mg. of lithium chloride is heated on the steam bath for 18 hours. The cooled solution is diluted with water and the resulting mixture is extracted with ether. The ether extract is washed with saline, dried with saline, dried with anhydrous magnesium sulfate and evaporated to dryness to give an oil. Chromatography on silica gel affords an oil; λ max. 5.78 μ (carbonyl groups).

Workup

  1. extractionthe resulting mixture is extracted with ether
  2. extractionThe ether extract
  3. washis washed with saline
  4. customdried with saline
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customevaporated to dryness
  7. customto give an oil
  8. customChromatography on silica gel affords an oil

Sources & evidence

ORD record
ord-7428934710db44b2aa3a2c48e94d734f
Source dataset
uspto-grants-1977_09
Patent number
US04046787

Reaction notes

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