Sodium methanesulfinate → HCID 10496371, compound

HRID 1585066Notes

Reaction equation

HRID 1585066 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:7][O:6][CH:5]([CH2:8][CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15](F)=[CH:14][CH:13]=2)=[O:11])[O:4][CH2:3]1.[Na+].[CH3:21][S:22]([O-:24])=[O:23]>CN(C)C=O>[CH3:1][C:2]1([CH3:19])[CH2:7][O:6][CH:5]([CH2:8][CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([S:22]([CH3:21])(=[O:24])=[O:23])=[CH:14][CH:13]=2)=[O:11])[O:4][CH2:3]1

Participants

4

Reactant 2

HCID 2733271Sodium methanesulfinateHCID 106354633-(5,5-Dimethyl-1,3-dioxan-2-yl)-1-(4-fluorophenyl)propan-1-one

Product 1

HCID 10496371HCID 10496371, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 3-(5,5-dimethyl-1,3-dioxan-2-yl)-1-(4-fluorophenyl)propan-1-one (Step 4) (1.68 g, 6.3 mmol) in dimethylformamide (75 ml), methanesulfinic acid sodium salt (2.9 g, 28.4 mmol) was added. The reaction mixture was heated at 120-30° C. for 72 hours. After cooling, the solvent was removed under reduced pressure and the reaction mixture was diluted with water. The material was extracted with methylene chloride and washed with brine. After drying (MgSO4), filtration and concentration, the crude solid (2.78 g) was purified by chromatography (silica gel, hexane/ethyl acetate, 6/4) to give the sulfone (1.62 g, 79%) as a white solid: mp (DSC) 104° C. Anal Calc'd. for C16H22SO5 : C, 58.88; H, 6.79; S, 9.82. Found: C, 58.76; H, 7.01; S, 10.21.

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 methylene chloride
  5. washwashed with brine
  6. customAfter drying
  7. filtration(MgSO4), filtration and concentration
  8. customthe crude solid (2.78 g) was purified by chromatography (silica gel, hexane/ethyl acetate, 6/4)

Sources & evidence

ORD record
ord-d049373e9de74301b8797aa47f73ff10
Source dataset
uspto-grants-1999_08
Patent number
US05935990

Reaction notes

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