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

HRID 351749

반응식

HRID 351749 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-10 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1e0a865ae353492d95932dc9687937af
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743802B2

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