Ethyl Acetate → 1-(3,5-Di-t-butylphenyl)butan-1-one

HRID 863383노트

반응식

HRID 863383 반응식
[C:1]([C:5]1[CH:6]=[C:7]([CH:15]([OH:19])[CH2:16][CH2:17][CH3:18])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].CCOC(C)=O>C(Cl)Cl.O=[Mn]=O>[C:1]([C:5]1[CH:6]=[C:7]([C:15](=[O:19])[CH2:16][CH2:17][CH3:18])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 2

HCID 8857Ethyl AcetateHCID 187050951-(3,5-Di-t-butylphenyl)butan-1-ol

생성물 1

HCID 187050871-(3,5-Di-t-butylphenyl)butan-1-one수율 40%

시약·촉매·용매 2

HCID 14801Manganese dioxide촉매HCID 6344Dichloromethane용매

실험 절차

To 2.37 g (9.05 mmol) of alcohol 19 in 18 mL of CH2Cl2 was added 7.86 g (90.45 mmol) of MnO2. The reaction mixture was stirred for 3 h, then filtered (celite over silica gel pad) and the pad was washed repeatedly with 20 mL aliquots of CH2Cl2. After concentration, ketone 20 was purified by chromatography (SiO2, 3% EtOAc-hexanes) to give 941 mg (3.62 mmol) of 20 (40% yield 1 Hz TLC (10% EtOAc-90% hexanes) Rf 0.7; 1H-NMR (CDCl3) δ1.01 (t, 3H, CH2CH3), 1.34 (s, 18H, 6(CH3)), 1.78 (m, 2H, CH2CH3), 2.96 (t, J=7 Hz, 2H, CH2CH2CH3), 7.63 (t, J=1 Hz, 1H, Ar-H), 7.83 (d, J=1 Hz, 2H, Ar-H).

후처리

  1. filtrationfiltered (celite over silica gel pad)
  2. washthe pad was washed repeatedly with 20 mL aliquots of CH2Cl2
  3. concentrationAfter concentration, ketone 20
  4. customwas purified by chromatography (SiO2, 3% EtOAc-hexanes)

출처 및 근거

ORD 기록
ord-1de789c184a5428e9d2ba7f3177c9e9d
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05721103

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