Methanol → 2-Cyano-2-methyl-7-methoxybenzo[1,4]benzodioxine

HRID 1866211Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1866211
B(F)(F)F.C[CH2:6][O:7][CH2:8][CH3:9].C([C@@:12]1([C:21]([O:23][CH3:24])=O)[CH2:16][C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[O:13]1)C.C[Si]([C:29]#[N:30])(C)C.[CH3:31]O>O>[C:29]([C:8]1([CH3:9])[O:7][C:6]2[C:17]3[CH:18]=[CH:19][CH:20]=[C:14]([O:13][CH3:31])[C:15]=3[CH:16]=[CH:12][C:21]=2[O:23][CH2:24]1)#[N:30]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 8000Boron trifluoride etherateHCID 82115Trimethylsilyl cyanideHCID 57358441Methyl (2s)-2-ethyl-2,3-dihydro-1-benzofuran-2-carboxylate

Produkt 1

HCID 686197232-Cyano-2-methyl-7-methoxybenzo[1,4]benzodioxineAusbeute 74,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Trifluoroboron etherate (mL, 9.6 mmol) was added to a solution of the product from Step 4 (1.0 g, 4.8 mmol), trimethylsilyl cyanide (2.5 mL, 9.6 mmol) in dichlorormethane (25 mL) cooled in a ice bath. The reaction was kept at 0 C for 1 h and warmed to 25 C over 30 min. Methanol (2.0 mL) was added, followed by addition of water (50 mL). After phase separation and extraction, the crude product was purified by chromatography on silica gel to give 0.73 g (74.8% yield) of the title compound.

Aufarbeitung

  1. temperaturecooled in a ice bath
  2. temperaturewarmed to 25 C over 30 min
  3. customAfter phase separation and extraction
  4. customthe crude product was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-d725b5b681cc4af7b54f3d28125fe814
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07629372B2

Notizen zur Reaktion

Wird geladen…