2-Fluoro-1-phenylethan-1-one → Methyl 3-methylbenzo[b]thiophene-2-carboxylate

HRID 241356Notes

Reaction equation

HRID 241356 reaction equation
[H-].[Na+].[C:3]([O:7][CH3:8])(=[O:6])[CH2:4][SH:5].F[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O>C1COCC1.CS(C)=O.O>[CH3:10][C:11]1[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[S:5][C:4]=1[C:3]([O:7][CH3:8])=[O:6]

Participants

7

Reactant 3

HCID 99472-Fluoro-1-phenylethan-1-oneHCID 16907Methyl ThioglycolateHCID 24758Sodium hydride

Product 1

HCID 268658Methyl 3-methylbenzo[b]thiophene-2-carboxylateYield 36%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 55% sodium hydride (390 mg, 9.69 mmol) in THF (7 mL)-DMSO (20 mL) was added methyl thioglycolate (0.64 ml) under N2 atmosphere. After ceasing of bubbling, the mixture was stirred for 15 minutes at room temperature, to which was added slowly a solution of 2-fluoroacetophenone (0.89 mL, 6.46 mmol) in DMSO (5 mL). The mixture was stirred at room temperature for 1 hour, diluted with water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was recrystallized from ethyl acetate/hexane to give the titled compound as a white crystal (533 mg, 36%).

Workup

  1. customof bubbling
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-85fd540bcc394a2ab65a26be9ede688e
Source dataset
uspto-grants-2014_02
Patent number
US08648208B2

Reaction notes

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