2-(3-Chlorophenyl)-2-methylpropanal → 3-(3-Chlorophenyl)-3-methylbutan-2-ol

HRID 83867노트

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HRID 83867 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:12])([CH3:11])[CH:9]=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH3:13][Mg+].[Br-]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:12])([CH3:11])[CH:9]([OH:10])[CH3:13])[CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 820751242-(3-Chlorophenyl)-2-methylpropanalHCID 178418689HCID 178418689, 화합물

생성물 1

HCID 667407143-(3-Chlorophenyl)-3-methylbutan-2-ol수율 78%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a stirred solution of 2-(3-chlorophenyl)-2-methylpropanal (4.6 g, 25.7 mmol) in THF (150 mL) at 0° C. was added MeMgBr (3M in ether, 17.1 mL, 51.3 mmol, 2 eq) dropwise over 2 h. After stirring 1 h at 0° C., the reaction was allowed to warm to room temperature, quenched with 1N HCl and then extracted with EtOAc. The extracts were dried over MgSO4 and evaporated in vacuo. The residue was purified by chromatography (silica, Hex/EtOAc=20:1 to 10:1) to give 3-(3-chlorophenyl)-3-methylbutan-2-ol (3.9 g, 78%). 1H NMR (400 MHz, CDCl3) δ 7.36 (s, 1H), 7.28 (m, 2H), 7.18 (m, 1H), 3.85 (q, 1H), 1.32 (d, J=6.4 Hz, 6H), 1.05 (d, J=6.8 Hz, 3H).

후처리

  1. temperatureto warm to room temperature
  2. customquenched with 1N HCl
  3. extractionextracted with EtOAc
  4. dry with materialThe extracts were dried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was purified by chromatography (silica, Hex/EtOAc=20:1 to 10:1)

출처 및 근거

ORD 기록
ord-1fac463ae16c490bb91b476bfa4fc554
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846739B2

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