Malonic Acid → (E)-3-(5-Bromothiophen-2-YL)acrylic acid

HRID 549280ノート

反応式

HRID 549280 の反応式
[C:1](O)(=O)[CH2:2][C:3]([OH:5])=[O:4].[Br:8][C:9]1[S:13][C:12](C=O)=[CH:11][CH:10]=1.N1CCCCC1>N1C=CC=CC=1>[Br:8][C:9]1[S:13][C:12](/[CH:1]=[CH:2]/[C:3]([OH:5])=[O:4])=[CH:11][CH:10]=1

参加物

5

反応物 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 784285-Bromothiophene-2-carbaldehyde

生成物 1

HCID 2059999(E)-3-(5-Bromothiophen-2-YL)acrylic acid

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
100 °C

実験手順

Malonic acid (44.40 g, 426.7 mmol) was added to a mixture of 5-bromothiophene-2-carbaldehyde (50 g, 261.7 mmol), piperidine (2.84 mL) and pyridine (150 mL). The mixture was refluxed for 1 h at 80° C. and than at 100° C. over night. The volatiles were evaporated and the residue was dissolved in water and acidified with hydrochloric acid (pH 2). The crude product was crystallized in ethanol. Yield: 55.24 g (90.5%). 1H NMR (270 MHz, CH3OH-d4) δ ppm 6.14 (d, J=15.83 Hz, 1H) 7.11-7.16 (m, 2H) 7.68 (d, J=16.36 Hz, 1H); MS 233.1 (M−H)+; Purity (HPLC) 94%.

後処理

  1. customThe volatiles were evaporated
  2. dissolutionthe residue was dissolved in water
  3. customThe crude product was crystallized in ethanol

出典と根拠

ORDレコード
ord-4fa273bc683840b1afd4a18cf9d455e1
出典データセット
uspto-grants-2011_05
特許番号
US07943639B2

反応ノート

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