Methanol → HCID 20029387, compound

A solution of 2.8 g of 2B in 5.4 ml of methyl acetate was added to 1 g of sodium hyride, and the mixture was heated at reflux for 7 hours, then 0.25 ml of methanol was added. When gas evolution ended, the mixture was heated at reflux for 15 minutes, then cooled and stirred at room temperature overnight. The mixture was quenched in water, the resulting mixture was acidified with glacial acetic acid, and extracted with methylene chloride. The extract was dried (MgSO4) and stripped of solvent. The residue was chromatographed on silica gel with a 1:3 v:v mixture of ethyl acetate and hexane as eluent. The middle fractions that were obtained gave ethyl 3-(4-methyl-3-isoxazolyl)-3-oxopropionate (2C), as a light yellow oil. 27 g of sodium methoxide was dissolved in a mixture of 100 ml of methanol and 100 ml of THF. 50 grams of aluminum oxide (activated, neutral, Brockmann I, Aldrich) was added and the mixture was stirred for 30 minutes. The solvents were removed under reduced pressure to give aluminum oxide-supported sodium-methoxide (2D).

1. temperaturethe mixture was heated
2. temperatureat reflux for 7 hours
3. temperaturethe mixture was heated
4. temperatureat reflux for 15 minutes
5. temperaturecooled
6. customThe mixture was quenched in water
7. extractionextracted with methylene chloride
8. dry with materialThe extract was dried (MgSO4)
9. customThe residue was chromatographed on silica gel with a 1:3 v
10. additionv mixture of ethyl acetate and hexane as eluent
11. customThe middle fractions that were obtained

ORD record

ord-c8b29cf6c3e245bd875f8fb6a28076b2

Source dataset

uspto-grants-1989_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04853027