Sodium hydride → HCID 68784837, compound

HRID 2266525Notes

Reaction equation

[H-].[Na+].[CH3:3][CH2:4][C:5](=[O:11])[CH2:6][C:7](=[O:10])[CH2:8][CH3:9].Br[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1>CN(C)C=O.O>[CH3:23][S:20]([C:17]1[CH:18]=[CH:19][C:14]([CH2:13][CH:6]([C:5](=[O:11])[CH2:4][CH3:3])[C:7](=[O:10])[CH2:8][CH3:9])=[CH:15][CH:16]=1)(=[O:21])=[O:22]

Participants

Conditions

Temperature: 5 °C

Procedure

Sodium hydride (60% in oil, 0.17 g) was added portionwise to a stirred solution of heptane-3,5-dione (0.54 mL) in N,N-dimethylformamide (4.0 mL) at 0-10° C. The resulting mixture was stirred at 0-10° C. for 10 minutes and then a solution of 1-bromomethyl-4-methanesulfonylbenzene (1.2 g) in N,N-dimethylformamide (2.0 mL) was added dropwise. The resulting mixture was stirred at room temperature for 18 hours, diluted with water and extracted with ethyl acetate. The combined extracts were washed with water and saturated aqueous sodium chloride solution and 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 by volume) gave title compound as a white solid, 0.61 g.

Workup

stirringThe resulting mixture was stirred at room temperature for 18 hours
extractionextracted 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 by volume)

Sources & evidence

ORD record: ord-e1ffe61854fc42ebbae98f6b66d8d7f7
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858640B2

Reaction notes

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