Triethylamine → Ethyl-1-(4-methoxynaphthylsulfonyl)-2,3-dihydroindole-3-acetate

HRID 1174527ノート

反応式

HRID 1174527 の反応式
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([S:13](Cl)(=[O:15])=[O:14])=[CH:5][CH:4]=1.[CH2:17]([O:19][C:20](=[O:31])[CH2:21][CH:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH2:23]1)[CH3:18].C(N(CC)CC)C>ClCCl.O>[CH2:17]([O:19][C:20](=[O:31])[CH2:21][CH:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]([S:13]([C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)(=[O:15])=[O:14])[CH2:23]1)[CH3:18]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 167755014-Methoxynaphthalene-1-sulfonyl chlorideHCID 21795444Ethyl (2,3-dihydro-1H-indol-3-yl)acetate

生成物 1

HCID 68773619Ethyl-1-(4-methoxynaphthylsulfonyl)-2,3-dihydroindole-3-acetate収率 94%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

4-Methoxynaphthylsulfonyl chloride (1.25 g, 5 mmol.) was added portionwise to ethyl-2,3-dihydro-1H indole-3-acetate (1 g, 5 mmol) in dichloromethane (20 cm3), containing triethylamine (1 cm3, 7 mmol) at 0° C. After stirring at room temperature for 4 h, the reaction was diluted with water and the organic layer was separated, dried and concentrated to give ethyl-1-(4-methoxynaphthylsulfonyl)-2,3-dihydroindole-3-acetate as an oil (2 g, 4.7 mmol, 94%). This was then taken up in ethyl alcohol (20 cm3) and aqueous sodium hydroxide (4N, 7 cm3, 28 mmol) was added and the resulting mixture was stirred and heated together at reflux for 2 h. The reaction mixture was then cooled and the ethyl alcohol was removed under reduced pressure. The residue was taken up in water and extracted once with diethyl ether to remove any unreacted ester. The aqueous mixture was then acidified and the product extracted into ethyl acetate. The organic layer was separated, dried and concentrated to provide 1-(4-methoxynaphthylsulfonyl)-2,3-dihydro-indole-3-acetic acid as a solid (1.17 g, 3.00 mmol, 64%).

後処理

  1. customthe organic layer was separated
  2. customdried
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-07e7d90f43c7492f9c820b04ff0bd081
出典データセット
uspto-grants-2010_11
特許番号
US07838518B2

反応ノート

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