Sodium Bicarbonate → 1-(5-Hydroxy-6,7-dimethyl-benzofuran-2-yl)-2-morpholin-4-yl-ethanone

HRID 480981ノート

反応式

HRID 480981 の反応式
[CH3:1][C:2]1[C:19]([O:20]C(=O)C)=[CH:18][C:5]2[CH:6]=[C:7]([C:9](=[O:17])[CH2:10][N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[O:8][C:4]=2[C:3]=1[CH3:24].C(=O)(O)[O-].[Na+]>CO>[OH:20][C:19]1[C:2]([CH3:1])=[C:3]([CH3:24])[C:4]2[O:8][C:7]([C:9](=[O:17])[CH2:10][N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:6][C:5]=2[CH:18]=1

参加物

4

反応物 2

HCID 516892Sodium BicarbonateHCID 10236780Acetic acid 6,7-dimethyl-2-(2-morpholin-4-yl-acetyl)-benzofuran-5-yl ester

生成物 1

HCID 102364101-(5-Hydroxy-6,7-dimethyl-benzofuran-2-yl)-2-morpholin-4-yl-ethanone収率 54.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of acetic acid 6,7-dimethyl-2-(2-morpholin4-yl-acetyl)-benzofuran-5-yl ester (23 mg), prepared as in Example 17, in MeOH (10 mL) was stirred while sodium bicarbonate (10 mg) was added. Then the mixture was stirred at RT overnight, followed by evaporation to dryness. The residue was purified by silica gel column, eluting with 5% MeOH in dichloromethane to give 11 mg of 1-(5-hydroxy-6,7-dimethyl-benzofuran-2-yl)-2-morpholin-4-yl-ethanone as an oil. Conversion into HCl salt gave a yellow solid. 1H NMR (CD3OD, 300 MHz) δ: 7.60 (s, 1H), 7.20 (s, 1H), 3.78 (m, 6H), 2.64 (m, 4H), 2.50 (s, 3H), 2.40 (s, 3H) ppm. 13C NMR (CDCl3, 75 MHz) δ: 187.98, 170.20, 153.31, 152.29, 146.58, 130.44, 124.53, 122.80, 114.36, 113.15, 64.69, 53.79, 21.28, 13.47, 12.86 ppm. M/S 290 (M+H+).

後処理

  1. additionwas added
  2. customfollowed by evaporation to dryness
  3. customThe residue was purified by silica gel column
  4. washeluting with 5% MeOH in dichloromethane

出典と根拠

ORDレコード
ord-0342f01a9fa946ce88315252eda02b97
出典データセット
uspto-grants-2003_11
特許番号
US06653346B1

反応ノート

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