Sodium hydride → HCID 19935465, compound

HRID 37414Notes

Reaction equation

HRID 37414 reaction equation
C(OP(OCC)([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][CH:8]=1)=O)C.[H-].[Na+].[H][H].[CH3:25][C:26]([C:28]1[CH:29]=[CH:30][C:31]2[S:37][CH2:36][C:35]([CH3:39])([CH3:38])[CH2:34][CH2:33][C:32]=2[CH:40]=1)=O>CN(C)C=O>[CH3:38][C:35]1([CH3:39])[CH2:34][CH2:33][C:32]2[CH:40]=[C:28](/[C:26](/[CH3:25])=[CH:6]/[C:7]3[CH:8]=[CH:9][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:12]=3)[CH:29]=[CH:30][C:31]=2[S:37][CH2:36]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 10979490Ethyl 4-((diethoxyphosphoryl)methyl)benzoateHCID 19935468HCID 19935468, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19935465HCID 19935465, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8.85 g of ethyl α-(diethoxyphosphinyl)-p-toluate were slowly added dropwise to 1.3 g of sodium hydride (50% in mineral oil) in 28 ml of dimethylformamide. The reaction mixture was stirred at room temperature until the evolution of hydrogen had finished. Thereafter, 4.2 g of 2,3,4,5-tetrahydro-3,3-dimethyl-benzothiepin-7-yl methyl ketone were added and the reaction mixture was stirred at room temperature for 2 hours. Thereafter, the mixture was poured on to ice/sodium chloride, extracted with ether, the ethereal solution was washed with water and dried and evaporated. Chromatography on silica gel (petroleum ether/ethyl acetate (95:5)) and recrystallization from hexane yielded ethyl p-[(E)-2-(2,3,4,5-tetrahydro-3,3-dimethyl-1-benzothiepin-7-yl)propenyl]benzoate of melting point 96°-97° C.

Workup

  1. extractionextracted with ether
  2. washthe ethereal solution was washed with water
  3. customdried
  4. customevaporated
  5. customChromatography on silica gel (petroleum ether/ethyl acetate (95:5)) and recrystallization from hexane

Sources & evidence

ORD record
ord-8ea14b2c581a406aa0794b18864fbfa3
Source dataset
uspto-grants-1995_05
Patent number
US05420273

Reaction notes

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