Acetone → HCID 23130548, compound

HRID 2080134Notes

Reaction equation

HRID 2080134 reaction equation
C(OP([CH2:9][C:10]1[S:11][C:12]([Br:15])=[CH:13][CH:14]=1)(=O)OCC)C.[H-].[Na+].[CH3:18][C:19]([CH3:21])=O.O>O1CCCC1>[Br:15][C:12]1[S:11][C:10]([CH:9]=[C:19]([CH3:21])[CH3:18])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 24758Sodium hydrideHCID 10710282HCID 10710282, compound

Product 1

HCID 23130548HCID 23130548, compoundYield 2.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(5-Bromothiophen-2-ylmethyl)phosphonic acid diethyl ester described in Preparation Example 142 (3.13 g, 10 mmol) was dissolved in tetrahydrofuran (20 mL), sodium hydride (0.40 g, 10 mmol, 60% in oil) was added to this solution under stirring at room temperature. The solution was stirred for 30 minutes at 60° C., then, acetone (1 g, 17.2 mmol) was added, and the solution was further stirred for 30 minutes. Water (100 mL) was added to the reaction solution, which was then extracted with hexane (50 mL), the organic layer was washed with water, dried over anhydrous magnesium sulfate, then, the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane), and the title compound (60 mg, 0.27 mmol, 2.7%) was obtained as a colorless oil.

Workup

  1. stirringThe solution was stirred for 30 minutes at 60° C.
  2. stirringthe solution was further stirred for 30 minutes
  3. extractionwas then extracted with hexane (50 mL)
  4. washthe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (hexane)

Sources & evidence

ORD record
ord-cfe899943bac42f9aad9af31e8b8e30e
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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