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ChemicalBook CAS DataBase List 2-methyloxan-4-one
1193-20-0

2-methyloxan-4-one synthesis

3synthesis methods
A solution of (2S)-2-methyltetrahydro-2H-pyran-4-ol (27.3 g, 235 mmol) in acetone (980 mL) was cooled in an ice bath and treated drop-wise with Jones reagent (2.5 M, 103 mL, 258 mmol). The reaction mixture was stirred for 10 minutes at 0 °C and then warmed to room temperature. After 30 minutes, the mixture was cooled to 0 °C. 2-Propanol (18 mL, 240 mmol) was added and stirred for 30 minutes. After the mixture had been concentrated in vacuo, the residue was partitioned between water and dichloromethane. The aqueous layer was extracted 3 times with dichloromethane, and the combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide the product 2-methyloxan-4-one.
2-methyl-tetrahydropyran-4-one
-

Yield:1193-20-0 57%

Reaction Conditions:

with hydrogen;palladium 10% on activated carbon in methanol at 20; for 72 h;

Steps:

4.b

1.35 g of 2 -methyl-2, 3-dihydropyran-4-one in 15 ml of ethyl acetate, in the presence of 270 mg of palladium-on-charcoal at 10%, are stirred under a hydrogen atmosphere at ambient temperature for 3 days. The reaction medium is filtered through filter paper and the filtrate is evaporated. The residue is chromatographed on silica gel, elution being carried out with 60/40 pentane/diethyl ether.787 mg of 2-methyltetrahydropyran-4-one are obtained in the form of a yellow oil. Yield = 57%.

References:

WO2010/63773,2010,A1 Location in patent:Page/Page column 20-21

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