Toluene → methyl (Z)-2-(2-oxotetrahydro-1H-1-pyrrolyl)-2-butenoate

HRID 51226

반응식

HRID 51226 반응식
O=[C:2]([CH2:7][CH3:8])[C:3]([O:5][CH3:6])=[O:4].C1(C)C=CC=CC=1.[NH:16]1[CH2:20][CH2:19][CH2:18][C:17]1=[O:21].O=P(Cl)(Cl)Cl>O>[O:21]=[C:17]1[CH2:18][CH2:19][CH2:20][N:16]1/[C:2](=[CH:7]\[CH3:8])/[C:3]([O:5][CH3:6])=[O:4]

참가 물질

6

반응물 4

HCID 1140TolueneHCID 120252-PyrrolidoneHCID 24813Phosphorus oxychlorideHCID 5451272-Ketobutyric acid methyl ester

생성물 1

HCID 59076257methyl (Z)-2-(2-oxotetrahydro-1H-1-pyrrolyl)-2-butenoate수율 60%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A 100 ml flask fitted with a magnetic stirring bar and a Dean-Stark trap was charged with methyl 2-oxobutanoate (7.5 g, 73 mmol), toluene (50 ml, 7 vol) and 2-pyrrolidinone (8.4 ml, 111 mmol, 1.5 equiv) followed by dropwise addition of POCl3 (1.6 ml, 20 mmol, 0.27 equiv). The reaction mixture was stirred under reflux with azeotropic removal of water via the Dean-Stask trap for 8 hours. After cooling down the solution was washed with 10% aq KHSO4 (2×3 vol). The aqueous phase was saturated with NaCl and back extracted with toluene (1×6 vol). The combined organic phase was dried over MgSO4, filtered and concentrated in vacuo to afford crude material (7.5 g) as an orange mobile oil. The crude oil was distilled (92-94° C., 0.1 mm Hg) and gave pure product (4.7 g, 60%) as a colourless oil.

후처리

  1. customA 100 ml flask fitted with a magnetic stirring bar
  2. temperatureAfter cooling down the solution
  3. washwas washed with 10% aq KHSO4 (2×3 vol)
  4. extractionback extracted with toluene (1×6 vol)
  5. dry with materialThe combined organic phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford crude material (7.5 g) as an orange mobile oil
  9. distillationThe crude oil was distilled (92-94° C., 0.1 mm Hg)

출처 및 근거

ORD 기록
ord-fbe9a53636c443c3a630486f6d995943
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713635B2

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