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Ethyl 4-fluoro-gamma,zeta-dioxobenzeneheptanoate → Ethyl 4-(methylsulfonyl)-gamma,zeta-dioxobenzeneheptanoate

HRID 1585073
Notes
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Reaction equation

HRID 1585073 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])[CH2:9][CH2:10][C:11](=[O:19])[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4][CH:3]=1.[Na].[CH3:22][S:23]([OH:25])=[O:24]>CN(C=O)C>[CH3:22][S:23]([C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])[CH2:9][CH2:10][C:11](=[O:19])[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4][CH:3]=1)(=[O:25])=[O:24]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 10564686Ethyl 4-fluoro-gamma,zeta-dioxobenzeneheptanoateHCID 16212824Methanesulfinic acid sodium

Product 1

HCID 10807067Ethyl 4-(methylsulfonyl)-gamma,zeta-dioxobenzeneheptanoateYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
82.5 °C

Procedure

To a solution of ethyl 4-fluoro-γ,ζ-dioxobenzeneheptanoate (Step 2) (870 mg, 3.1 mmol) in DMF (25 ml), methanesulfinic acid sodium (1.27 g, 12.4 mmol) was added. The reaction mixture was heated at 130-35° C. for 30 hours. After cooling, the solvent was removed under reduced pressure and the reaction mixture was diluted with water. The material was extracted with ethyl acetate and washed with brine. After drying (MgSO4), filtration and concentration, the crude dark brown solid (840 mg) was purified by chromatography (silica gel, hexane/ethyl acetate, 1/1) to give the sulfone (270 mg, 26%) as a white solid: mp (DSC) 97° C. Anal Calc'd. for C16H20SO6 : C, 56.46; H, 5.92; S, 9.42. Found: C, 56.56; H, 6.10; S, 9.62.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed under reduced pressure
  3. additionthe reaction mixture was diluted with water
  4. extractionThe material was extracted with ethyl acetate
  5. washwashed with brine
  6. customAfter drying
  7. filtration(MgSO4), filtration and concentration
  8. customthe crude dark brown solid (840 mg) was purified by chromatography (silica gel, hexane/ethyl acetate, 1/1)

Sources & evidence

ORD record
ord-aad1715692a7446da1a53e642a7d7ea1
Source dataset
uspto-grants-1999_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05935990

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes