Nitromethane → Methyl 3-methyl-4-nitrobutanoate

HRID 1732275

반응식

HRID 1732275 반응식
N12CCCCC1C=NCCC2.[N+:12]([CH3:15])([O-:14])=[O:13].[C:16]([O:21][CH3:22])(=[O:20])/[CH:17]=[CH:18]/[CH3:19]>CO>[CH3:19][CH:18]([CH2:15][N+:12]([O-:14])=[O:13])[CH2:17][C:16]([O:21][CH3:22])=[O:20]

참가 물질

5

반응물 3

HCID 6375NitromethaneHCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 638132Methyl Crotonate

생성물 1

HCID 13633418Methyl 3-methyl-4-nitrobutanoate수율 66.2%

시약·촉매·용매 1

HCID 887Methanol용매2회

반응 조건

온도
60 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-a57ec767445d4b49a721c5bb2fc48ac2
출처 데이터셋
uspto-grants-1980_12
특허 번호
US04237054

연결된 노트

불러오는 중…