Water → Ethyl 2-(E-2-(4-(N,N-dimethylaminomethyl)phenyl)ethen-1-yl)benzoate

HRID 1178191

反応式

HRID 1178191 の反応式
Br[C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:13][N:14]([CH2:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[CH2:22])=[CH:19][CH:18]=1)[CH3:15].C(N(CC)CC)C.O>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[CH3:15][N:14]([CH2:16][C:17]1[CH:18]=[CH:19][C:20](/[CH:21]=[CH:22]/[C:2]2[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:23][CH:24]=1)[CH3:13]

参加物

8

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 80186Ethyl 2-bromobenzoateHCID 519956Benzenemethanamine, ar-ethenyl-N,N-dimethyl-

生成物 1

HCID 11120439Ethyl 2-(E-2-(4-(N,N-dimethylaminomethyl)phenyl)ethen-1-yl)benzoate収率 63.5%

試薬・触媒・溶媒 3

HCID 80271Tri-o-tolylphosphine触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
140 °C

実験手順

18.8 g (82 mmol) of ethyl 2-bromobenzoate, 17.2 g (107 mmol) of 4-(N,N,-dimethylaminomethyl)styrene [sic], 20.7 g (205 mmol) of triethylamine, 0.36 g of palladium(II) acetate and 0.96 g of tri(o-tolyl)phosphine were mixed in 200 ml of dimethylformamide and, after addition of 1 ml of water, stirred at 140° C. for 3 h. The reaction mixture was then concentrated in vacuo, and the resulting residue was partitioned between ethyl acetate and water. The organic phase was separated off, washed with water, dried and concentrated in vacuo. The residue was then recrystallized from petroleum ether. 16.1 g (63%) of the product were obtained.

後処理

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe resulting residue was partitioned between ethyl acetate and water
  3. customThe organic phase was separated off
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was then recrystallized from petroleum ether

出典と根拠

ORDレコード
ord-a9a0313d536d42f6b5d99083604a5221
出典データセット
uspto-grants-2007_10
特許番号
US07276500B2

関連ノート

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