Ammonium Hydroxide → 2-{4-[2-(Tetrahydropyran-2-yloxy)ethoxy]benzofur-7-yl}acetamide

HRID 751490ノート

反応式

HRID 751490 の反応式
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][O:10][C:11]1[C:16]2[CH:17]=[CH:18][O:19][C:15]=2[C:14]([CH2:20][C:21]([OH:23])=O)=[CH:13][CH:12]=1.[OH-].[NH4+:25]>O1CCCC1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][O:10][C:11]1[C:16]2[CH:17]=[CH:18][O:19][C:15]=2[C:14]([CH2:20][C:21]([NH2:25])=[O:23])=[CH:13][CH:12]=1

参加物

4

反応物 2

HCID 14923Ammonium HydroxideHCID 69270245{4-[2-(Tetrahydropyran-2-yloxy)ethoxy]benzofur-7-yl}acetic acid

生成物 1

HCID 692676922-{4-[2-(Tetrahydropyran-2-yloxy)ethoxy]benzofur-7-yl}acetamide収率 80%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Combine {4-[2-(Tetrahydropyran-2-yloxy)ethoxy]benzofur-7-yl}acetic acid (0.920 g, 2.872 mmol), and 1,1-carbonyldiimidazole (2.365 g, 14.585 mmol) in tetrahydrofuran (15 ml), and stir for 1 hour under nitrogen. Cool the mixture to 0° C., and add concentrated aqueous ammonium hydroxide (2 ml). Remove the ice bath, and stir the mixture at room temperature for 16 hours. Dilute the mixture with ethyl acetate, wash with water and brine, dry over sodium sulfate, filter, and concentrate. Purification using flash chromatography and eluting with hexane:ethyl acetate gives 0.732 g (80%) of the title product as a white solid. Mass spectrum: electrospray (m/z) 236 (M++1-85).

後処理

  1. customRemove the ice bath
  2. additionDilute the mixture with ethyl acetate
  3. washwash with water and brine
  4. dry with materialdry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurification
  8. washeluting with hexane

出典と根拠

ORDレコード
ord-16215c1e28164e1996bddbb55146c962
出典データセット
uspto-grants-2008_07
特許番号
US07405305B2

反応ノート

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