Sodium hydride → 3-(2-Chloro-4-methanesulfonylbenzyl)pentane-2,4-dione

HRID 2266516Notes

Reaction equation

[H-].[Na+].[CH3:3][C:4](=[O:9])[CH2:5][C:6](=[O:8])[CH3:7].Br[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][C:13]=1[Cl:22]>CN(C)C=O.O>[Cl:22][C:13]1[CH:14]=[C:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:16]=[CH:17][C:12]=1[CH2:11][CH:5]([C:4](=[O:9])[CH3:3])[C:6](=[O:8])[CH3:7]

Participants

Conditions

Temperature: 5 °C

Procedure

Sodium hydride (60% in oil, 0.30 g) was added portionwise to a stirred solution of pentane-2,4-dione (0.92 g) in N,N-dimethylformamide (8.0 mL) at 0-10° C. The resulting mixture was stirred at 0-10° C. for 20 minutes and then a solution of 1-bromomethyl-2-chloro-4-methanesulfonylbenzene (2.0 g) in N,N-dimethylformamide (3.0 mL) was added dropwise. The resulting mixture was stirred at room temperature for 5 hours, and then diluted with water and this mixture was extracted with ethyl acetate. The combined extracts were washed with water and 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 ethyl acetate and cyclohexane (1:4 to 3:7 by volume) gave title compound as a white solid, 1.2 g.

Workup

stirringThe resulting mixture was stirred at room temperature for 5 hours
extractionthis mixture was extracted with ethyl acetate
washThe combined extracts were washed with water and saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulfate
customThe solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel
washeluting with a mixture of ethyl acetate and cyclohexane (1:4 to 3:7 by volume)

Sources & evidence

ORD record: ord-56875cfe997044d4bfbbd75f7663832e
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858640B2

Reaction notes

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