[3-(Tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-(3,5-dimethoxyphenyl)-methanol → [3-(Tert-butyldimethylsilanyloxy)-4-methoxyphenyl]-(3,5-dimethoxyphenyl)methanone

HRID 2378253ノート

反応式

HRID 2378253 の反応式
[C:1]([Si:5]([CH3:28])([CH3:27])[O:6][C:7]1[CH:8]=[C:9]([CH:15]([C:17]2[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[C:19]([O:25][CH3:26])[CH:18]=2)[OH:16])[CH:10]=[CH:11][C:12]=1[O:13][CH3:14])([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[C:1]([Si:5]([CH3:28])([CH3:27])[O:6][C:7]1[CH:8]=[C:9]([C:15]([C:17]2[CH:18]=[C:19]([O:25][CH3:26])[CH:20]=[C:21]([O:23][CH3:24])[CH:22]=2)=[O:16])[CH:10]=[CH:11][C:12]=1[O:13][CH3:14])([CH3:3])([CH3:2])[CH3:4]

参加物

4

反応物 1

HCID 69204033[3-(Tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-(3,5-dimethoxyphenyl)-methanol

生成物 1

HCID 69204700[3-(Tert-butyldimethylsilanyloxy)-4-methoxyphenyl]-(3,5-dimethoxyphenyl)methanone収率 99%

試薬・触媒・溶媒 2

HCID 178418406HCID 178418406、化合物触媒2 回HCID 6344Dichloromethane溶媒

実験手順

To a solution of [3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-(3,5-dimethoxy-phenyl)-methanol (13.1 g, 32.4 mmol) in CH2Cl2 (330 mL) was added manganese dioxide (13.0 g, 150.0 mmol), and the mixture was stirred at ambient temperature for 8 h. Manganese dioxide (13.0 g, 150.0 mmol) was again added, and stirring proceeded for an additional 16 h. The mixture was filtered through Celite, and the sicciate was washed with CH2Cl2 (50 mL). The filtrate was evaporated, providing [3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-(3,5-dimethoxy-phenyl)-methanone as an oil (12.9 g, 99% yield): 1H NMR (CDCl3) δ 0.18 (s, 6H, 2SiCH3), 1.00 (s, 9H, SiC(CH3)3), 3.83 (s, 6H, 2OCH3), 3.89 (s, 3H, OCH3), 6.65 (t, J=2.4 Hz, 1H, Ar), 6.86-6.90 (m, 3H, Ar), 7.39-7.47 (m, 2H, Ar).

後処理

  1. stirringstirring
  2. waitproceeded for an additional 16 h
  3. filtrationThe mixture was filtered through Celite
  4. washthe sicciate was washed with CH2Cl2 (50 mL)
  5. customThe filtrate was evaporated

出典と根拠

ORDレコード
ord-4e5bc64bddcc46d7bbbc194f184f5c53
出典データセット
uspto-grants-2008_12
特許番号
US07470723B2

反応ノート

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