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

HRID 351749

反応式

HRID 351749 の反応式
[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

参加物

5

反応物 3

HCID 793352-Acetyl-5-bromothiopheneHCID 22635083Tetrahydrofuran tolueneHCID 178418573HCID 178418573、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-10 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1e0a865ae353492d95932dc9687937af
出典データセット
uspto-grants-2004_06
特許番号
US06743802B2

関連ノート

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