Acetone → 1-Benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidone

HRID 2166619ノート

反応式

HRID 2166619 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH:10]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([CH3:29])([CH3:28])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:17][C:16]=2[O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=O.S(=O)(=O)(O)O.[OH-].[NH4+]>[O-2].[O-2].[O-2].[Cr+6].C(O)(=O)C.O>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([CH3:28])([CH3:29])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:17][C:16]=2[O:30][CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

8

反応物 4

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 204997751-Benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinol

生成物 1

HCID 204997831-Benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidone

試薬・触媒・溶媒 3

HCID 10219390chromium (VI) trioxide触媒HCID 176Acetic Acid溶媒HCID 962Water溶媒

反応条件

温度
18 °C

実験手順

To a cooled solution of 24.8 g. (50 mmols.) of 1-benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinol, 100 ml. of acetone, 6.0 g. (60 mmols.) of chromium trioxide, 15 ml. of water and 20 ml. of acetic acid is added dropwise 20 ml. of concentrated sulfuric acid at such a rate as to maintain the temperature at 5° C. The reaction mixture is stirred 5 hours longer (t<18° C.) and then neutralized with concentrated ammonium hydroxide. The reaction mixture is extracted with 500 ml. of ether, the ether extract washed once with saturated sodium chloride, dried over magnesium sulfate and evaporated Purification is accomplished via rapid column chromatography on 100 g. of silica gel eluted with ether to yield the title compound.

後処理

  1. extractionThe reaction mixture is extracted with 500 ml
  2. extractionof ether, the ether extract
  3. washwashed once with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customPurification
  7. washof silica gel eluted with ether

出典と根拠

ORDレコード
ord-e66addc1db514811bc4654553dc336d0
出典データセット
uspto-grants-1983_06
特許番号
US04387229

反応ノート

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