Dimethyl Sulfate → HCID 86759321, compound

HRID 1840670Notes

Reaction equation

C[C:2](=[O:9])[C:3](=NO)[C:4](=O)[CH3:5].S([O:15][CH3:16])(OC)(=O)=O.[C:17](=O)([O-])[O-].[K+].[K+].[CH2:23]([NH:25][CH2:26]C)C>COC(C)(C)C.CN(C)C=O>[CH3:23][N:25]([CH:2]=[O:9])[CH3:26].[CH3:17][C:4]([O:15][CH3:16])([CH3:3])[CH3:5]

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 129.0 g of pentane-2,3,4-trione 3-oxime in 385 g of MTBE and 138.7 g of dimethyl sulfate (DMS) were added dropwise to a suspension of 165 g of potassium carbonate in a mixture of 100 g of dimethylformamide (DMF) and 300 g of tert-butyl methyl ether (MTBE) at about 20° C. with cooling. After stirring at about 20° C. for 2 h, 21.9 g of diethylamine were added to destroy excess DMS and, after stirring at about 20° C. for a further hour, 800 ml of water were added. The solution was extracted with tert-butyl methyl ether. From the combined organic phases there were obtained after washing with 1 N H2SO4 144.6 g of pentane-2,3,4-trione 3-O-methyloxime (96.5% pure according to GC analysis), corresponding to a yield of 97.6% of theory.

Workup

temperaturewith cooling
customto destroy excess DMS
stirringafter stirring at about 20° C. for a further hour
addition800 ml of water were added
extractionThe solution was extracted with tert-butyl methyl ether
customFrom the combined organic phases there were obtained
washafter washing with 1 N H2SO4 144.6 g of pentane-2,3,4-trione 3-O-methyloxime (96.5% pure according to GC analysis), corresponding to a yield of 97.6% of theory

Sources & evidence

ORD record: ord-eb3c9fa7f4d746e18109aa3c2b11e5dc
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06680410B2

Reaction notes

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