Benzaldehyde → 2-Benzylidene-1,3-indandione

HRID 2113930

반응식

HRID 2113930 반응식
[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

참가 물질

6

반응물 3

HCID 240BenzaldehydeHCID 1233581,2-IndandioneHCID 6327189Boron monoxide

생성물 1

HCID 2378222-Benzylidene-1,3-indandione

시약·촉매·용매 2

HCID 8082Piperidine촉매HCID 241Benzene용매

실험 절차

(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, 2H), 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.

후처리

  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

출처 및 근거

ORD 기록
ord-7b48657b4ae94f3b95e234a05fade6d7
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432303B2

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