Water → 3-Formylbut-2-enyl acetate

To a solution of 4-acetoxy-2-methyl-2-buten-1-ol (6.69 g, 46.4 mmol) in dimethylformamide (40 ml) were added 2,2,6,6-tetramethyl-piperidine-1-oxy (0.39 g, 2.32 mmol, 5 mol %) and cuprous chloride (0.48 g, 4.64 mmol, 10 mol %). The mixture was subjected to reaction at 40° C. for 8 hours while bubbling oxygen at a rate of about 100 ml/min. After completion of the reaction, the reaction mixture was poured into ice-cooled water (30 ml) and extracted with ether (100 ml) three times. The extract was dried over anhydrous magnesium sulfate. Evaporation of the ether followed by purification by column chromatography (ethyl acetate-hexane (=1:3)) gave 4-acetoxy-2-methyl-2-buten-1-al (6.02 g, 42.3 mmol; Yield: 91.2%).

1. customThe mixture was subjected to reaction at 40° C. for 8 hours
2. customwhile bubbling oxygen at a rate of about 100 ml/min
3. customAfter completion of the reaction
4. additionthe reaction mixture was poured into ice-
5. extractionextracted with ether (100 ml) three times
6. dry with materialThe extract was dried over anhydrous magnesium sulfate
7. customEvaporation of the ether
8. customfollowed by purification by column chromatography (ethyl acetate-hexane (=1:3))

ORDレコード

ord-81e0ab3abfbe4e8fbf8e7f4e5262a06e

出典データセット

uspto-grants-1996_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05527952