Selenious Acid → 5-Chloro-4-ethoxycarbonylmethyl-2-formyl-indole-1-carboxylic acid methyl ester

HRID 1161887

反応式

HRID 1161887 の反応式
[CH3:1][O:2][C:3]([N:5]1[C:13]2[C:8](=[C:9]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:10]([Cl:14])=[CH:11][CH:12]=2)[CH:7]=[C:6]1[CH3:21])=[O:4].[Se](O)(O)=[O:23]>O1CCOCC1.CCOC(C)=O>[CH3:1][O:2][C:3]([N:5]1[C:13]2[C:8](=[C:9]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:10]([Cl:14])=[CH:11][CH:12]=2)[CH:7]=[C:6]1[CH:21]=[O:23])=[O:4]

参加物

5

反応物 2

HCID 1091Selenious AcidHCID 668201565-Chloro-4-ethoxycarbonylmethyl-2-methyl-indole-1-carboxylic acid methyl ester

生成物 1

HCID 866038735-Chloro-4-ethoxycarbonylmethyl-2-formyl-indole-1-carboxylic acid methyl ester

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

5-Chloro-4-ethoxycarbonylmethyl-2-methyl-indole-1-carboxylic acid methyl ester (398 mg, 1.28 mmol) is dissolved under an atmosphere of argon in dioxane (18 ml). Selenious acid (331 mg, 2.56 mmol) is added, and the reaction mixture is heated to 100° C. for 18 hours. TLC analysis indicates complete conversion of the starting material. The reaction mixture is diluted with EtOAc and poured on water. The organic layer is washed with saturated aqueous NaCl solution, dried over Na2SO4 and concentrated. The solid residue is purified by FCC (hexane/EtOAc 2:1) to afford the title compound. 1H NMR (DMSO, 400 MHz) δ 1.20 (t, J=6.6 Hz, 3H), 4.09 (s, 3H), 4.12 (q, J=6.6 Hz, 2H), 4.19 (s, 2H), 7.64 (d, J=10.8, 1H), 8.09 (d, J=10.8, 1H), 10.32 (s, 1H); ES-MS: 346.1.1 [M+Na]+.

後処理

  1. additionpoured on water
  2. washThe organic layer is washed with saturated aqueous NaCl solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe solid residue is purified by FCC (hexane/EtOAc 2:1)

出典と根拠

ORDレコード
ord-8fa564b97d724679a1570eb4d623a91f
出典データセット
uspto-grants-2010_10
特許番号
US07820672B2

関連ノート

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