2-Acetyl-5-bromothiophene → 5-Bromo-alpha,alpha-dimethyl-2-thiophenemethanol

HRID 351749

Reaktionsgleichung

Reaktionsgleichung von HRID 351749
[C:1]([C:4]1[S:5][C:6]([Br:9])=[CH:7][CH:8]=1)(=[O:3])[CH3:2].[CH3:10][Mg]Br.C1(C)C=CC=CC=1.C1COCC1>C1COCC1>[Br:9][C:6]1[S:5][C:4]([C:1]([OH:3])([CH3:10])[CH3:2])=[CH:8][CH:7]=1

Komponenten

5

Edukt 3

HCID 793352-Acetyl-5-bromothiopheneHCID 22635083Tetrahydrofuran tolueneHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 227143025-Bromo-alpha,alpha-dimethyl-2-thiophenemethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

To a solution of 2-acetyl-5-bromothiophene in THF (2.5 mL/mmol) at −30° C. was added 1.4M methylmagnesium bromide in 3:1 toluene-THF (1.5 eq) and the resulting mixture was warmed to −10° C. and stirred for 1.5 hours. After quenching with saturated aqueous ammonium chloride solution, the mixture was partitioned between ether and water. The organic fraction was dried and evaporated, and the crude material was chromatographed on silica gel eluting with a 1:4 mixture of ether and hexane to afford the 2-bromo-5-(1-hydroxy-1-methylethyl)thiophene compound.

Aufarbeitung

  1. customAfter quenching with saturated aqueous ammonium chloride solution
  2. customthe mixture was partitioned between ether and water
  3. customThe organic fraction was dried
  4. customevaporated
  5. customthe crude material was chromatographed on silica gel eluting with a 1:4 mixture of ether and hexane

Quellen und Nachweise

ORD-Eintrag
ord-1e0a865ae353492d95932dc9687937af
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743802B2

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