Diethyl Ether → HCID 19024388, compound

HRID 1033731Notes

Reaction equation

HRID 1033731 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][SH:12])=[CH:7][CH:6]=1.Br[C:14]([CH3:26])([CH3:25])[C:15]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=1[F:24])=[O:16].C(OCC)C>C1COCC1.CCCCCC.O>[F:24][C:18]1[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=1[C:15](=[O:16])[C:14]([S:12][CH2:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH3:3])=[CH:6][CH:7]=1)([CH3:25])[CH3:26]

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 804074-Methoxy-alpha-toluenethiolHCID 152640192-Bromo-1-(2,4-difluorophenyl)-2-methyl-1-propanone

Product 1

HCID 19024388HCID 19024388, compoundYield 100.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

In 180 ml of THF was suspended 2.4 g (60 mmol) of 60% sodium hydride having been washed with hexane, and 9.4 g (61 mmol) of 4-methoxy-α-toluenethiol was added dropwise to the suspension while stirring under ice-cooling. After being stirred for 10 minutes, the mixture was added dropwise to a solution of 15.0 g (57 mmol) of 2-bromo-1-(2,4-difluorophenyl)-2-methylpropan-1-one in 225 ml of THF with stirring under ice-cooling. To the reaction mixture were added diethyl ether and water, and the organic layer was separated, washed with water and then with a saturated sodium chloride aqueous solution, and dried. The solvent was removed by distillation under reduced pressure, and the residue was subjected to column chromatography using a mixed solvent of hexane and ethyl acetate (10:1). The solvent was removed by distillation under reduced pressure to obtain 19.2 g (95%) of 1-(2,4-difluorophenyl)-2-((4-methoxyphenyl)methylthio)-2-methylpropan-1-one as a colorless oily substance.

Workup

  1. additionwas added dropwise to the suspension
  2. temperaturecooling
  3. stirringAfter being stirred for 10 minutes
  4. stirringwith stirring under ice-
  5. temperaturecooling
  6. customthe organic layer was separated
  7. washwashed with water
  8. dry with materialwith a saturated sodium chloride aqueous solution, and dried
  9. customThe solvent was removed by distillation under reduced pressure
  10. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-3777a4e6c7f544be872e15e0a13c7ef1
Source dataset
uspto-grants-1994_05
Patent number
US05312815

Reaction notes

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