Ethyl Acetate → Methyl 4-(2-formylphenylthio)butyrate

HRID 413581Notes

Reaction equation

HRID 413581 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].[SH:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21].C(OCC)(=O)C>CN(C)C=O>[CH:4]([C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[S:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[O:5]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 67970o-FluorobenzaldehydeHCID 11332495Methyl 4-sulfanylbutanoate

Product 1

HCID 11413730Methyl 4-(2-formylphenylthio)butyrateYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under an argon atmosphere, 2-fluorobenzaldehyde (3 g) was dissolved in 9 ml of dimethylformamide and potassium carbonate (5.01 g) was added. Methyl 4-mercaptobutyrate (4.5 ml) was added at room temperature and-was stirred at room temperature for 14 hours. After the addition of 50 ml of ethyl acetate, the mixture was washed with 30 ml of water twice, 3 ml of a 1N hydrochloric acid, and 30 ml of water three times. After drying with anhydrous sodium sulfate, the mixture was concentrated. The concentrated matter was subjected to silica gel chromatography (hexane/ethyl acetate=6/1) purification. The resulting effective fractions were concentrated to yield methyl 4-(2-formylphenylthio)butyrate (5.45 g, Yield 95%).

Workup

  1. washthe mixture was washed with 30 ml of water twice
  2. dry with materialAfter drying with anhydrous sodium sulfate
  3. concentrationthe mixture was concentrated
  4. customThe concentrated matter was subjected to silica gel chromatography (hexane/ethyl acetate=6/1) purification
  5. concentrationThe resulting effective fractions were concentrated

Sources & evidence

ORD record
ord-49e61231f5be4cec897988809330f817
Source dataset
uspto-grants-2003_05
Patent number
US06566535B1

Reaction notes

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