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

HRID 751490Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 751490
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-16215c1e28164e1996bddbb55146c962
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405305B2

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