5-Methoxy-1H-indole-2-carbaldehyde → Benzyl (2E)-3-(5-methoxy-1H-indol-2-yl)-2-propenoate

HRID 11010

반응식

HRID 11010 반응식
C1(P(=[CH:20][C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:31][O:32][C:33]1[CH:34]=[C:35]2[C:39](=[CH:40][CH:41]=1)[NH:38][C:37]([CH:42]=O)=[CH:36]2>C(Cl)Cl>[CH3:31][O:32][C:33]1[CH:34]=[C:35]2[C:39](=[CH:40][CH:41]=1)[NH:38][C:37](/[CH:42]=[CH:20]/[C:21]([O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:22])=[CH:36]2

참가 물질

4

반응물 2

HCID 8264565-Methoxy-1H-indole-2-carbaldehydeHCID 3862746Benzyl 2-(triphenyl-lambda5-phosphanylidene)acetate

생성물 1

HCID 11843433Benzyl (2E)-3-(5-methoxy-1H-indol-2-yl)-2-propenoate수율 87%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Benzyl (triphenylphosphoranylidene)acetate (49.2 g, 0.120 mol) was added to a stirred solution of 5-methoxy-1H-indole-2-carbaldehyde (1) (20.0 g, 0.114 mol) in CH2Cl2 (500 mL) and the solution was stirred at room temperature for 4 h. The solvent was removed in vacuo and the residue slurried with methanol (200 mL), whereupon crystallisation of the product occurred. The mixture was filtered, washed with several portions of cold methanol, and dried to give benzyl (2E)-3-(5-methoxy-1H-indol-2-yl)-2-propenoate (2) in a 30.46 g, 87% yield as pale yellow plates; mp 155–157° C. 1H NMR δ (CDCl3) 8.28 (s, 1H), 7.69 (d, J=16.1 Hz, 1H), 7.43–7.32 (m, 5H), 7.23 (d, J=9.1 Hz, 1H), 7.03 (d, J=2.3 Hz, 1H), 6.92 (dd, J=9.1, 2.3 Hz, 1H), 6.74 (d, J=1.8 Hz, 1H), 6.24 (d, J=16.1 Hz, 1H), 5.26 (s, 2H), 3.84 (s, 3H).Found: C, 74.45; H, 5.62; N, 4.58. C19H17NO3 requires C, 74.25; H, 5.57; N, 4.56.

후처리

  1. customThe solvent was removed in vacuo
  2. customthe residue slurried with methanol (200 mL), whereupon crystallisation of the product
  3. filtrationThe mixture was filtered
  4. washwashed with several portions of cold methanol
  5. customdried

출처 및 근거

ORD 기록
ord-526f417124d842ee909b2a74f393688d
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094798B1

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