Dichloromethane → 3-[2(E)-(2-Pyridyl)ethenyl]benzyl alcohol

HRID 1198565

Reaktionsgleichung

Reaktionsgleichung von HRID 1198565
ClC1C=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=3)[CH2:17][OH:18])=[N:9]2)=CC=1.CC(C[AlH]CC(C)C)C.ClCCl>C1(C)C=CC=CC=1>[N:9]1[CH:10]=[CH:5][CH:6]=[CH:7][C:8]=1/[CH:12]=[CH:13]/[C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17][OH:18]

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 14487Diisobutylaluminum hydrideHCID 10827738trans-3-[2-(7-Chloroquinolin-2-yl)ethenyl]benzyl alcohol

Produkt 1

HCID 703418553-[2(E)-(2-Pyridyl)ethenyl]benzyl alcohol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

The methyl benzoate (Example 37b part ii) (2.25 g, 9.4 mmol) was dissolved in dry toluene (60 ml) and cooled to -70° C. under nitrogen. 1M DIBAL in dichloromethane (18.8 ml, 18.8 mmol) was added over 15 minutes and the reaction mixture allowed to warm up to -30° C. for 30 minutes. The reaction was quenched by careful addition of methanol (8 ml), then water, and after filtration through Celite the organic phase was evaporated in vacuo.

Aufarbeitung

  1. temperatureto warm up to -30° C. for 30 minutes
  2. customThe reaction was quenched by careful addition of methanol (8 ml)
  3. filtrationwater, and after filtration through Celite the organic phase
  4. customwas evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f12ccb71f6ac4577a2b2f68c674ebacb
Quelldatensatz
uspto-grants-1994_01
Patentnummer
US05281593

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