Benzaldehyde → 2-Benzylidene-1,3-indandione

HRID 1071767

反応式

HRID 1071767 の反応式
[B]=O.[CH:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:11]1(=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][C:12]1=O>N1CCCCC1.C1C=CC=CC=1>[CH:13](=[C:12]1[C:3](=[O:10])[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:11]1=[O:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

6

反応物 3

HCID 240BenzaldehydeHCID 1233581,2-IndandioneHCID 6327189Boron monoxide

生成物 1

HCID 2378222-Benzylidene-1,3-indandione

試薬・触媒・溶媒 2

HCID 8082Piperidine触媒HCID 241Benzene溶媒

実験手順

(8) (Chem. Pharm. Bull. 1974, 22(2), 448-451). Boron oxide (720 mg, 10.26 mmol) and benzaldehyde (800 mg, 7.53 mmol) were added to a stirred solution of the indandione (1.00 g, 6.84 mmol) and piperidine (3 drops) in 10.2 ml of benzene. The solution was refluxed with stirring for 30 minutes. After filtration of the solution, the filtrate was concentrated under reduced pressure. The resulting crystalline solid was recrystallized from ethanol to afford 1.00 g (62.4%) of yellowish-green platelets: mp 149.5-150.0° C. (lit. mp 150° C., Okukawa, et al., Chem. Pharm. Bull., 1974, 22(2), 448-451). 1H NMR (250 MHz) δ 8.47-8.45 (m, 2 H), 8.06-7.99 (m, 2 H), 7.90 (s, 1 H), 7.84-7.79 (m, 2 H), 7.58-7.50 (m, 3 H); 13C NMR (62.7 MHz) 190.5, 189.2, 147.2, 142.7, 140.2, 135.6, 135.4, 134.3, 133.4, 133.2, 129.3, 129.0, 123.5, 123.5 ppm.

後処理

  1. temperatureThe solution was refluxed
  2. filtrationAfter filtration of the solution
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting crystalline solid was recrystallized from ethanol
  5. customto afford 1.00 g (62.4%) of yellowish-green platelets

出典と根拠

ORDレコード
ord-1a7df1ec91ff4c14866d69c7210e6156
出典データセット
uspto-grants-2005_06
特許番号
US06906105B2

関連ノート

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