Water → HCID 86584490、化合物

HRID 394942ノート

反応式

HRID 394942 の反応式
[CH3:1][C:2]([CH3:24])=[CH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:9][CH:8]=1)=[O:5].[Cl-].[Al+3].[Cl-].[Cl-].O>C(Cl)Cl>[CH3:24][C:2]1([CH3:1])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH:13]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]=2)[NH:6][C:4](=[O:5])[CH2:3]1

参加物

5

反応物 3

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 86584489HCID 86584489、化合物

生成物 1

HCID 86584490HCID 86584490、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

1 g of (RS)-ethyl 2-[4-(3,3-dimethylacrylamido)-phenyl]-heptanoate was dissolved in 10 ml of methylene chloride and treated with 1.2 g of aluminium chloride. The mixture was heated to reflux for 6 hours. The mixture was poured onto 25 ml of iced water and then was extracted with two portions of 25 ml of methylene chloride. The combined extracts were washed with two portion of 25 ml of saturated aqueous sodium bicarbonate solution and one portion of 25 ml of saturated aqueous sodium chloride solution. The organic phase was dried over MgSO4 and concentrated in vacuo. The product was purified by flash chromatography (SiO2, 20% ethyl acetate/hexanes). 1H NMR (CDCl3): 8.92 (br. s, 1H), 7.21 (d, J=1.9 Hz, 1H), 7.13 (dd, J=8.1, 1.9 Hz, 1H), 6.78 (d, J=8.1 Hz, 1H), 4.20-4.00 (m, 2H), 3.48 (t, J=7.7 Hz, 1H), 2.48 (s, 2H), 2.10-1.90 (m, 1H), 1.80-1.65 (m, 1H), 1.35-1.15 (m, 6H), 1.33 (s, 3H), 1.32 (s, 3H), 1.22 (t, J=7.1 Hz, 3H), 0.86 (t, J=6.6 Hz, 3H).

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 6 hours
  3. extractionwas extracted with two portions of 25 ml of methylene chloride
  4. washThe combined extracts were washed with two portion of 25 ml of saturated aqueous sodium bicarbonate solution and one portion of 25 ml of saturated aqueous sodium chloride solution
  5. dry with materialThe organic phase was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by flash chromatography (SiO2, 20% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-cbd0a16b0a994263834b79f6b9d35da5
出典データセット
uspto-grants-2003_08
特許番号
US06603012B2

反応ノート

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