Nitromethane → Methyl 3-methyl-4-nitrobutanoate

Temperatur

60 °C

1,5-Diazabicyclo[5,4,0]undec-5-ene (6 ml) is added to a solution of nitromethane (91.5 g) in methanol (500 ml). The resulting mixture is heated to 60° C. and methyl crotonate (100 g, 1 m) is added under nitrogen. The mixture is then stirred for 6 days at 60° C. after which it is cooled to room temperature and most of the methanol is removed in vacuo. The residue is treated with ether (500 ml) and washed with 2N hydrochloric acid (250 ml) and water (250 ml). The organic layer is dried (Na2SO4) and evaporated in vacuo to give crude product. The crude product is purified by column chromatography on silica gel (500 g, ethyl acetate/hexane 2:98) to give methyl 3-methyl-4-nitrobutanoate (106.6 g, 66%).

1. customis removed in vacuo
2. additionThe residue is treated with ether (500 ml)
3. washwashed with 2N hydrochloric acid (250 ml) and water (250 ml)
4. dry with materialThe organic layer is dried (Na2SO4)
5. customevaporated in vacuo
6. customto give crude product
7. customThe crude product is purified by column chromatography on silica gel (500 g, ethyl acetate/hexane 2:98)

ORD-Eintrag

ord-a57ec767445d4b49a721c5bb2fc48ac2

Quelldatensatz

uspto-grants-1980_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04237054