Dimethylformamide → 8-Methyl-2,3-dihydro-1,4-benzodioxin-6-carbaldehyde

HRID 639031Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 639031
Br[C:2]1[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=[C:4]([CH:12]=[O:13])[CH:3]=1.[CH3:14]N(C=O)C>[F-].[K+]>[CH3:14][C:2]1[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=[C:4]([CH:12]=[O:13])[CH:3]=1

Komponenten

4

Edukt 2

HCID 6228DimethylformamideHCID 166371768-Bromo-2,3-dihydro-1,4-benzodioxine-6-carbaldehyde

Produkt 1

HCID 451220228-Methyl-2,3-dihydro-1,4-benzodioxin-6-carbaldehydeAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 522689Potassium FluorideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 8-bromo-2,3-dihydro-1,4-benzodioxin-6-carbaldehyde (240 mg, 0.987 mmol) in DMF (5 mL) were added LiCL (126 mg, 2.96 mmol), Me Sn (0.137 mL, 0.987 mmol) and PdCL2(PPh)2 (35 mg, 0.049 mmol). After heated at 70° C. for 12 hr, the mixture was cooled down to room temperature and diluted with aqueous KF solution. The resulting solution was extracted several times with DCM. The organic parts were combined, concentrated and purified with column chromatography (silica, 10-40% Ethyl acetate in hexane) affording the title compound as an off-white solid (145 mg, 83%): MS (ES) m/z 179 (M+H)+.

Aufarbeitung

  1. temperaturethe mixture was cooled down to room temperature
  2. extractionThe resulting solution was extracted several times with DCM
  3. concentrationconcentrated
  4. custompurified with column chromatography (silica, 10-40% Ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d9d90dc5a40042f08d047cdbe41771eb
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691850B2

Notizen zur Reaktion

Wird geladen…