Sodium hydride → 3-Propyl-tetrahydrothiopyran-4-one-3-carboxylic acid

HRID 1638140Notes

Reaction equation

HRID 1638140 reaction equation
[S:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH:3]([C:8]([OH:10])=[O:9])[CH2:2]1.[H-].[Na+].I[CH2:14][CH2:15][CH3:16]>CN(C)C=O.O>[CH2:14]([C:3]1([C:8]([OH:10])=[O:9])[C:4](=[O:7])[CH2:5][CH2:6][S:1][CH2:2]1)[CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 22617731Tetrahydrothiopyran-4-one-3-carboxylic acid

Product 1

HCID 226177553-Propyl-tetrahydrothiopyran-4-one-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of tetrahydrothiopyran-4-one-3-carboxylic acid, allyl ester (1.0 g, 5 mmol) in 1 mL of dimethylformamide was added to a stirred mixture of sodium hydride (60% in oil, 0.2.2 g, 5.5 mmol) and 1-iodopropane (0.934 g, 5.5 mmol) in 2.5 mL of dimethylformarnmide at 0° C. The reaction mixture was warmed to room temperature and stirred overnight. The reaction mixture was diluted with water and extracted with ether. The etheral layer was washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo and the residue purified by flash column chromatography on silica gel eluted with hexane:ether (19:1) to give 0.277 g of 3-propyl-tetrahydrothiopyran-4-one-3-carboxylic acid, allyl ester.

Workup

  1. extractionextracted with ether
  2. washThe etheral layer was washed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed in vacuo
  5. customthe residue purified by flash column chromatography on silica gel
  6. washeluted with hexane:ether (19:1)

Sources & evidence

ORD record
ord-d81bcbb9dc89420c8b5785bdf870a7ac
Source dataset
uspto-grants-2000_03
Patent number
US06043358

Reaction notes

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