Malonic Acid → 3-(1-Benzothiophen-3-yl)prop-2-enoic acid

HRID 1177755ノート

反応式

HRID 1177755 の反応式
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH:10]=O)=[CH:2]1.C(O)(=O)[CH2:13][C:14]([OH:16])=[O:15].N1CCCCC1>N1C=CC=CC=1>[S:1]1[CH:2]=[C:3]([CH:10]=[CH:13][C:14]([OH:16])=[O:15])[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]1=2

参加物

5

反応物 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 2273281-Benzothiophene-3-carbaldehyde

生成物 1

HCID 534270043-(1-Benzothiophen-3-yl)prop-2-enoic acid

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
110 °C

実験手順

A suspension of 1-benzothiophene-3-carbaldehyde (4.9 g, 0.03 mol), malonic acid (6.6 g, 0.06 mol) and piperidine (1 mL) in 100 mL anhydrous pyridine was heated at 110° C. overnight. The reaction mixture was cooled to room temperature and the solvent was removed in vacuo. The residue was taken up in 100 mL of water and 1 N hydrochloric acid was added to adjust the pH of this solution to ca. 3. The suspension was filtered and the yellow solid was collected, washed with water (3×50 mL) and concentrated in vacuo to give the indicated product with 95% purity (5.65 g, 91%).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe solvent was removed in vacuo
  3. addition1 N hydrochloric acid was added
  4. filtrationThe suspension was filtered
  5. customthe yellow solid was collected
  6. washwashed with water (3×50 mL)
  7. concentrationconcentrated in vacuo
  8. customto give the indicated product with 95% purity (5.65 g, 91%)

出典と根拠

ORDレコード
ord-ae439ab614e24076a77c548e13f71740
出典データセット
uspto-grants-2010_11
特許番号
US07842808B2

反応ノート

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