Diisobutylaluminum hydride → 5-Bromo-2-(2-thienylmethoxy)benzenemethanol

HRID 1455967Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1455967
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[C:6]([CH:11]=1)[C:7](OC)=[O:8].CC(C[AlH]CC(C)C)C>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[C:6]([CH:11]=1)[CH2:7][OH:8]

Komponenten

4

Edukt 2

HCID 14487Diisobutylaluminum hydrideHCID 22105630Methyl 5-bromo-2-(2-thienylmethoxy)benzoate

Produkt 1

HCID 289814405-Bromo-2-(2-thienylmethoxy)benzenemethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-50 °C

Versuchsvorschrift

A solution of methyl 5-bromo-2-(2-thienylmethoxy)benzoate (1.6 g, 4.9 mmol) in dichloromethane (20 ml) was cooled to -85° C. A solution of DIBAL (5.8 ml, 1N in CH2Cl2) was added dropwise. The temperature was maintained below -75° C. for 30 minutes and then warmed to -50° C. over 21/2% hours. The reaction mixture was quenched with 1N HCl, washed with aqueous sodium hydrogen carbonate solution, dried (MgSO4) and evaporated. The product was purified by chromatography (eluant: diethyl ether/hexane) to give 5-bromo-2-(2-thienylmethoxy)benzyl alcohol a colourless gum (0.53 g, 36.4%).

Aufarbeitung

  1. temperatureThe temperature was maintained below -75° C. for 30 minutes
  2. customThe reaction mixture was quenched with 1N HCl
  3. washwashed with aqueous sodium hydrogen carbonate solution
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe product was purified by chromatography (eluant: diethyl ether/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-e53d125e41db434381ce0c3b6a668494
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05843942

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