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

HRID 11010

反応式

HRID 11010 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-526f417124d842ee909b2a74f393688d
出典データセット
uspto-grants-2006_08
特許番号
US07094798B1

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