Hydrochloric Acid → 3-{[4-(Difluoromethoxy)phenyl]ethynyl}benzaldehyde

HRID 30551

Reaktionsgleichung

Reaktionsgleichung von HRID 30551
[F:1][CH:2]([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:13]=[C:14]([CH:18]3OCC[O:19]3)[CH:15]=[CH:16][CH:17]=2)=[CH:6][CH:5]=1.C1COCC1.Cl>O>[F:1][CH:2]([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=2)[CH:18]=[O:19])=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 597903012-(3-{[4-(Difluoromethoxy)phenyl]ethynyl}phenyl)-1,3-dioxolane

Produkt 1

HCID 574358553-{[4-(Difluoromethoxy)phenyl]ethynyl}benzaldehydeAusbeute 432,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Into a mixture of 2-(3-{[4-(difluoromethoxy)phenyl]ethynyl}phenyl)-1,3-dioxolane, (1.0 g, 3.1 mmol) and THF (5 mL) was added HCl (2N, 1 mL). The mixture was stirred at room temperature for 2 hours, poured into water and extracted with EtOAc/ethyl ether 1/1. The organic extracts were dried over MgSO4. Evaporation and purification on silica gel (ISCO) using hexanes/EtOAc (3/1) as the eluting solvents gave 3-{[4-(difluoromethoxy)phenyl]ethynyl}benzaldehyde as a yellow oil (3.65 g, 95% yield), MS m/e M+ 272; 1H NMR (400 MHz, DMSO-d6) 3.9-4.05 (m, 4H), 5.72 (s, 1H), 7.1-7.3 (m, 4H), 7.62 (m, 2H), 7.8-7.9 (m, 2H), 8.03 (s, 1H), 9.99 (s, 1H).

Aufarbeitung

  1. extractionextracted with EtOAc/ethyl ether 1/1
  2. dry with materialThe organic extracts were dried over MgSO4
  3. customEvaporation and purification on silica gel (ISCO)

Quellen und Nachweise

ORD-Eintrag
ord-6d9370bc6fab4c8ba5e07a254eae4b49
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423158B2

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