Dimethylformamide → 5-Dimethylamino-3-ethoxycarbonyl-2-methoxycarbonyl-penta-2,4-dienoic acid methyl ester

HRID 919710노트

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HRID 919710 반응식
[CH3:1][O:2][C:3](=[O:16])[C:4]([C:12]([O:14][CH3:15])=[O:13])=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:6].CO[CH:19](OC)[N:20]([CH3:22])[CH3:21].CN(C=O)C>C1C=CC=CC=1>[CH3:15][O:14][C:12](=[O:13])[C:4]([C:3]([O:2][CH3:1])=[O:16])=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:6]=[CH:19][N:20]([CH3:22])[CH3:21]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 78373Dimethylformamide dimethyl acetalHCID 867141093-Ethoxycarbonyl-2-methoxycarbonyl-but-2-enoic acid methyl ester

생성물 1

HCID 851589875-Dimethylamino-3-ethoxycarbonyl-2-methoxycarbonyl-penta-2,4-dienoic acid methyl ester수율 85.4%

시약·촉매·용매 1

HCID 241Benzene용매

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온도
80 °C

실험 절차

A mixture of 3-ethoxycarbonyl-2-methoxycarbonyl-but-2-enoic acid methyl ester (10 g, 43.5 mmol), dimethylformamide dimethyl acetal (6.1 mL, 45.7 mmol) and DMF (8 mL) was heated at 80° C. for 3 h. The slightly cooled solution was poured into 100 mL of benzene, and the resulting mixture was washed several times with water. The organic layer was dried over MgSO4 and concentrated to give a dark yellow solid, which was recrystallized from CCl4 to give 10.6 g of the title compound as a bright yellow solid. 1H NMR (CDCl3, 200 MHz): δ=6.77 (d, 1H, J=12.8 Hz), 5.74 (d, 1H, J=13.2 Hz), 4.34 (q, 2H, J=7.0 Hz), 3.80 (s, 3H), 3.71 (s, 3H), 2.97 (br s, 6H), 1.36 (t, 3H, J=7.0 Hz).

후처리

  1. washthe resulting mixture was washed several times with water
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customto give a dark yellow solid, which
  5. customwas recrystallized from CCl4

출처 및 근거

ORD 기록
ord-174b9e1c1338406b9b70b38992e1d1ef
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09271970B2

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