Dimethylformamide → 3-[2-(Tetrahydropyran-2-yloxy)-ethyl]-benzaldehyde

HRID 553306Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 553306
Br[C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.CN(C)[CH:24]=[O:25]>O1CCCC1>[O:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH:11]1[O:10][CH2:9][CH2:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[CH:24]=[O:25]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 184035082-(3-bromophenethoxy)tetrahydro-2H-pyranHCID 178418339Butyllithium

Produkt 1

HCID 866183253-[2-(Tetrahydropyran-2-yloxy)-ethyl]-benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 2-[2-(3-bromo-phenyl)-ethoxy]-tetrahydro-pyran (20 g) in anhydrous tetrahydrofuran (300 mL) at −78° C. was added n-butyl lithium (2.5M in hexanes, 33.6 ml) dropwise over 5 minutes. The dark solution was kept at −78° C. for 30 minutes then N,N-dimethylformamide (16.35 ml) was added. The mixture was stirred −78° C. for half hour then quenched with aqueous ammonium acetate, and allowed to warm to room temperature. The resulting mixture was extracted with ethyl acetate, and the organics washed with brine, dried over sodium sulfate and concentrated in vacuo to give a yellow/orange oil (16.0 g). The material was used in the next step without further purification.

Aufarbeitung

  1. customthen quenched with aqueous ammonium acetate
  2. temperatureto warm to room temperature
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. washthe organics washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-74163d73a7f2464db5a855bcb4245f60
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951954B2

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