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

HRID 1627352노트

반응식

HRID 1627352 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

반응 조건

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-4d1f1d9589984f93979134ecd65f163e
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785488B2

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