Sodium hydride → 2-(6-Ethoxypyridin-3-yl)acetic acid

HRID 1796466ノート

反応式

HRID 1796466 の反応式
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH3:12][CH2:13][O-:14].[Na+].[H-].[Na+]>CCO>[CH2:13]([O:14][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1)[CH3:12]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 2723922Sodium ethoxideHCID 140715712-(6-Chloropyridin-3-yl)acetic acid

生成物 1

HCID 221813682-(6-Ethoxypyridin-3-yl)acetic acid収率 82%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒3 回

反応条件

温度
100 °C

実験手順

To a stirred solution of (6-chloro-3-pyridinyl)acetic acid (0.094 g, 0.545 mmol) in EtOH (1.6 mL) was added 3.1 M EtONa in EtOH (0.7 mL, 2.17 mmol) and the reaction mixture was stirred at 100° C. room temperature for 24 hours after which an excess of NaH (60% dispersion in oil) was added together with 1 mL EtOH and heating at 100° C. was continued for 96 h. The solvent was evaporated in vacuo and the residue was taken up into diethyl ether (5 mL). The organic phase was washed with diluted HCl (2×2 mL) and brine (2 mL), dried over MgSO4, filtered, and concentrated in vacuo to provide the title compound (0.081 g, 82%) as a pale brown solid, which was used without further purification. 1H NMR (CDCl3): δ 10.06 (br s, 1H), 8.06 (s, 1H), 7.55 (d, J=9.2 Hz, 1H), 6.72 (d, J=8.4 Hz, 1H), 4.30 (q, J=6.1 Hz, 2H), 3.58 (s, 2H) 1.38 (t, J=8.0, 3H). MS (ESI) (M+H)+=182.

後処理

  1. customThe solvent was evaporated in vacuo
  2. washThe organic phase was washed with diluted HCl (2×2 mL) and brine (2 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-253930cc86e54e0cb4b0cb21b6083e9c
出典データセット
uspto-grants-2006_04
特許番号
US07030139B2

反応ノート

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