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

HRID 1585073Notes

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]

Participants

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

temperatureAfter cooling
customthe solvent was removed under reduced pressure
additionthe reaction mixture was diluted with water
extractionThe material was extracted with ethyl acetate
washwashed with brine
customAfter drying
filtration(MgSO4), filtration and concentration
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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