Triethylamine → Methyl 2-(4-(cyanomethyl)benzyl)-3-oxobutanoate

HRID 445045ノート

反応式

HRID 445045 の反応式
[OH:1][CH:2]([CH3:9])[C:3](=[CH2:8])[C:4]([O:6][CH3:7])=[O:5].Br[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]#[N:19])=[CH:13][CH:12]=1.C(N(CC)CC)C>C(#N)C.C1(C)C=CC=CC=1.O>[C:18]([CH2:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:8][CH:3]([C:2](=[O:1])[CH3:9])[C:4]([O:6][CH3:7])=[O:5])=[CH:12][CH:13]=1)#[N:19]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 27914Benzeneacetonitrile, 4-bromo-HCID 5080248Methyl 3-hydroxy-2-methylen-butanoat

生成物 1

HCID 59590640Methyl 2-(4-(cyanomethyl)benzyl)-3-oxobutanoate

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

A stirred mixture of methyl 3-hydroxy-2-methylenebutanoate (70.0 g), 2-(4-bromophenyl)acetonitrile (126.5 g), PdCl2[P(o-tol)3]2 (4.2 g) and triethylamine (108.9 g) in acetonitrile (280 mL) was heated under nitrogen at 70° C. for 6 hours. The mixture was cooled to room temperature, diluted with toluene (840 mL) and water (840 mL) and stirred for 10 minutes. The organic layer was separated, washed with water (840 mL) and concentrated under reduced pressure to give the subtitle compound as a red oil, 158.7 g. This product was used in the next step without further purification.

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with water (840 mL)
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-a8d6376f78754e45938942e10dfc0e61
出典データセット
uspto-grants-2013_07
特許番号
US08476288B2

反応ノート

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