Hydrochloric Acid → Ethyl 4-(methylsulfonyl)-β-oxobenzenepropanoate

HRID 1610675Notes

Reaction equation

HRID 1610675 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH3:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)=[O:3].[C:14](=O)([O:18]CC)[O:15][CH2:16][CH3:17].[H-].[Na+].Cl>C(O)C>[CH3:13][S:10]([C:7]1[CH:6]=[CH:5][C:4]([C:2](=[O:3])[CH2:1][C:14]([O:15][CH2:16][CH3:17])=[O:18])=[CH:9][CH:8]=1)(=[O:12])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 825294-Methylsulfonylacetophenone

Product 1

HCID 22142993Ethyl 4-(methylsulfonyl)-β-oxobenzenepropanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixed solution of 4-(methylsulfonyl)acetophenone (10 g, 42.2 mmol), ethanol (0.2 ml) and diethyl carbonate (50 ml) was added sodium hydride (3.37 g, 60% in oil, 84.4 mmol) by small portions at room and the mixture was stirred temperature for 2 hrs. and at 60° C. for 1 hr. The reaction solution was cooled, 1N hydrochloric acid (30 ml) was added and the mixture was extracted with ethyl acetate (100 ml). The extract was washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=3:1) to give the objective substance (3.76 g, 33%) as crystals.

Workup

  1. waitand at 60° C. for 1 hr
  2. temperatureThe reaction solution was cooled
  3. extractionthe mixture was extracted with ethyl acetate (100 ml)
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=3:1)
  8. customto give the objective substance (3.76 g, 33%) as crystals

Sources & evidence

ORD record
ord-8b0b410809a04cc59d66fe8482080081
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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