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

HRID 751490노트

반응식

HRID 751490 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-16215c1e28164e1996bddbb55146c962
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405305B2

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