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

HRID 2287451ノート

反応式

HRID 2287451 の反応式
[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]>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]

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 14801Manganese dioxide触媒HCID 6344Dichloromethane溶媒

実験手順

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): TLC (10% EtOAc-90% hexanes) Rf 0.7; 1H-NMR (CDCl3)δ 1.01 (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).

後処理

  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)

出典と根拠

ORDレコード
ord-4d5e393dd29b4c6caa0298b471983e64
出典データセット
uspto-grants-2000_07
特許番号
US06083977

反応ノート

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