Sodium hydride → HCID 68786995, compound

HRID 2266461Notes

Reaction equation

HRID 2266461 reaction equation
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5].[H-].[Na+].Br[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1>CN(C)C=O.Cl>[CH3:21][S:18]([C:15]1[CH:16]=[CH:17][C:12]([CH2:11][CH:3]([C:2](=[O:7])[CH3:1])[C:4](=[O:6])[CH3:5])=[CH:13][CH:14]=1)(=[O:19])=[O:20]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 31261AcetylacetoneHCID 27335814-(Methylsulfonyl)benzyl Bromide

Product 1

HCID 68786995HCID 68786995, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent3×

Procedure

A solution of pentane-2,4-dione (4.4 g) in N,N-dimethylformamide (10 mL) was added dropwise over a period of 15 minutes to a stirred suspension of sodium hydride (60% in oil, 1.7 g) in N,N-dimethylformamide (50 mL) at −5° C. The mixture was warmed to room temperature over 20 minutes and a solution of 1-bromomethyl-4-methanesulfonylbenzene (10 g) in N,N-dimethylformamide (20 mL) was added dropwise over a period of 10 minutes. The resulting mixture was stirred at room temperature for 17 hours and then diluted with 1.0 M aqueous hydrochloric acid (100 mL). The resulting mixture was extracted with a mixture of diethyl ether and ethyl acetate (1:1 by volume) and the combined extracts washed with a saturated aqueous sodium chloride solution and then dried over magnesium sulfate. The solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (2:1 to 1:2 by volume) gave title compound as a colourless gum, 3.7 g.

Workup

  1. extractionThe resulting mixture was extracted with a mixture of diethyl ether and ethyl acetate (1:1 by volume)
  2. washthe combined extracts washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel
  5. washeluting with a mixture of cyclohexane and ethyl acetate (2:1 to 1:2 by volume)

Sources & evidence

ORD record
ord-9dc15408b5c1401d9eddb3a343b84071
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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