Ammonia → 2-(6-Hydroxymethyl-benzofuran-3-yl)-acetamide

HRID 222462ノート

反応式

HRID 222462 の反応式
C([O:3][C:4](=O)[CH2:5][C:6]1[C:10]2[CH:11]=[CH:12][C:13]([CH2:15][O:16]C(=O)C)=[CH:14][C:9]=2[O:8][CH:7]=1)C.[NH3:21]>>[OH:16][CH2:15][C:13]1[CH:12]=[CH:11][C:10]2[C:6]([CH2:5][C:4]([NH2:21])=[O:3])=[CH:7][O:8][C:9]=2[CH:14]=1

参加物

3

反応物 2

HCID 222Ammonia2 回HCID 68523733(6-Acetoxymethyl-benzofuran-3-yl)-acetic acid ethyl ester

生成物 1

HCID 685240552-(6-Hydroxymethyl-benzofuran-3-yl)-acetamide

反応条件

温度
60 °C

実験手順

(6-Acetoxymethyl-benzofuran-3-yl)-acetic acid ethyl ester (0.80 g, 2.90 mmol) was added to liquid ammonia at −78° C., the reaction flask was sealed and heated at 60° C. for 6 days. The reaction mixture was cooled, the excess of ammonia was allowed to evaporate and the residue was washed with in hexane and precipitated to give the 2-(6-hydroxymethyl-benzofuran-3-yl)-acetamide as an off white solid (0.54 g, 90%). 1H NMR (DMSO-d6, 400 MHz) 3.46 (s, 2H), 4.60 (d, J=5.6 Hz, 1H), 5.25 (t, J=5.6 Hz, 1H), 6.98 (brs, 1H), 7.20 (d, J=8.0 Hz, 1H), 7.47 (s, 1H), 7.53 (brs, 1H), 7.56 (d, J=8.0 Hz, 1H), 7.77 (s, 1H), 13C NMR (DMSO-d6, 400 MHz) 30.8, 63.4, 109.4, 115.4, 120.0, 121.6, 127.0, 139.9, 143.4, 155.2, 171.7.

後処理

  1. customthe reaction flask was sealed
  2. temperatureThe reaction mixture was cooled
  3. customto evaporate
  4. washthe residue was washed with in hexane
  5. customprecipitated

出典と根拠

ORDレコード
ord-fc6dd6b82b9c43998ddec132e85726b3
出典データセット
uspto-grants-2012_06
特許番号
US08207216B2

反応ノート

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