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

HRID 919710ノート

反応式

HRID 919710 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-174b9e1c1338406b9b70b38992e1d1ef
出典データセット
uspto-grants-2016_03
特許番号
US09271970B2

反応ノート

読み込み中…