Imidazole → (R)-1-Cyclohexyl-1-phenyl-1-trimethylsiloxy-2-propanone

HRID 1087663ノート

反応式

HRID 1087663 の反応式
[CH3:1][Si:2](Cl)([CH3:4])[CH3:3].N1C=CN=C1.[CH:11]1([C@@:17]([OH:27])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18](=[O:20])[CH3:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.CCOCC>CN(C=O)C>[CH:21]1([C@:17]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)([O:27][Si:2]([CH3:4])([CH3:3])[CH3:1])[C:18](=[O:20])[CH3:19])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

参加物

6

反応物 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 6397ChlorotrimethylsilaneHCID 15030055(R)-1-cyclohexyl-1-hydroxy-1-phenyl-2-propanone

生成物 1

HCID 15105836(R)-1-Cyclohexyl-1-phenyl-1-trimethylsiloxy-2-propanone収率 68.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

To a solution of 12 ml (95 mmoles) of trimethylsilyl chloride and 11.6 g (172 mmoles) of imidazole in 100 ml of DMF was added 20 g (86 mmoles) of (R)-1-cyclohexyl-1-hydroxy-1-phenyl-2-propanone. This mixture was heated to 85° C. overnight. The next day, the mixture was cooled and poured onto a mixture of 100 ml of petroleum ether and 100 ml of ether. This was extracted with water. The organic layer was separated, dried, and the solvent removed. The residue was chromatographed on silica gel with hexane as the eluent to give 18.0 g of clear oil. IR 2950, 1730 cm-1NMR (CDCl3) δ7.4(m, 5H), 2.3(t, 1H), 2.1(s, 3H), 1.9-1.0(m, 10H), 0.3(s, 9H).

後処理

  1. temperatureThe next day, the mixture was cooled
  2. extractionThis was extracted with water
  3. customThe organic layer was separated
  4. customdried
  5. customthe solvent removed
  6. customThe residue was chromatographed on silica gel with hexane as the eluent

出典と根拠

ORDレコード
ord-1cbaa38756074c26b8232498e55e5dbe
出典データセット
uspto-grants-1991_07
特許番号
US05036107

反応ノート

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