3-Pyridinecarboxaldehyde → 2-[(3-Pyridyl)hydroxymethyl]-6-(2-methyl-1,3-dioxolan-2-yl)naphthalene

HRID 35191Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 35191
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]3([CH3:17])[O:16][CH2:15][CH2:14][O:13]3)[CH:8]=2)[CH:3]=1.C([Li])(C)(C)C.[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]=[O:30])[CH:24]=1>O1CCCC1>[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]([OH:30])[C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[C:7]([C:12]4([CH3:17])[O:16][CH2:15][CH2:14][O:13]4)[CH:8]=3)[CH:3]=2)[CH:24]=1

Komponenten

5

Edukt 3

HCID 103713-PyridinecarboxaldehydeHCID 136879082-(6-Bromonaphthalen-2-yl)-2-methyl-1,3-dioxolaneHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 156122412-[(3-Pyridyl)hydroxymethyl]-6-(2-methyl-1,3-dioxolan-2-yl)naphthaleneAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 4.5 g of 2-bromo-6-(2-methyl-1,3-dioxolan-2-yl)naphthalene in 30 ml of tetrahydrofuran was cooled to -78° C. under nitrogen, and 14.0 ml of 2.2M t-butyl lithium added dropwise. A solution of 1.64 g of 3-pyridinecarboxaldehyde in 15 ml of tetrahydrofuran was added over a period of 10 minutes, and the temperature was allowed to rise to -20° C. during the next 30 minutes. The reaction was quenched with 30 ml of water and the mixture extracted with methylene chloride. The organic layer was dried over sodium sulfate and solvent removed under reduced pressure to give a solid that was recrystallized from methylene chloride/diethyl ether to give 3.1 g of 2-[(3-pyridyl)hydroxymethyl]-6-(2-methyl-1,3-dioxolan-2-yl)naphthalene, m.p. 154°-156° C.

Aufarbeitung

  1. customto rise to -20° C. during the next 30 minutes
  2. customThe reaction was quenched with 30 ml of water
  3. extractionthe mixture extracted with methylene chloride
  4. dry with materialThe organic layer was dried over sodium sulfate and solvent
  5. customremoved under reduced pressure
  6. customto give a solid
  7. customthat was recrystallized from methylene chloride/diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-91ab7496c7d048febe8a88218f6c8816
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04766127

Notizen zur Reaktion

Wird geladen…