Pyridine → 1-(2,2,4-trimethyl-cyclohex-3-enyl)-ethanone O-methyl-oxime

HRID 42729

反応式

HRID 42729 の反応式
[CH3:1][C:2]1([CH3:12])[CH:7]=[C:6]([CH3:8])[CH2:5][CH2:4][CH:3]1[C:9](=O)[CH3:10].N1C=CC=CC=1.Cl.[CH3:20][O:21][NH2:22]>CO>[CH3:20][O:21][N:22]=[C:9]([CH:3]1[CH2:4][CH2:5][C:6]([CH3:8])=[CH:7][C:2]1([CH3:12])[CH3:1])[CH3:10]

参加物

5

反応物 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 30169881-(2,2,4-Trimethyl-3-cyclohexen-1-yl)ethan-1-one

生成物 1

HCID 866753381-(2,2,4-trimethyl-cyclohex-3-enyl)-ethanone O-methyl-oxime収率 92.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
24 °C

実験手順

To a stirred solution of 1-(2,2,4-trimethyl-cyclohex-3-enyl)-ethanone (162 g; 0.97 mol), prepared as described in example P4, in methanol (500 ml) was added pyridine (160 ml; 1.95 mol) followed by a portionwise addition of methoxyamine hydrochloride (142 g; 1.70 mol). The reaction mixture was stirred at 24° C. for 16 hours under nitrogen atmosphere. Methanol was removed under reduced pressure, the residue poured in water (600 ml) and 1N hydrochloric acid was added (100 ml). The solution was extracted with dichloromethane (3×300 ml). Combined organic layers were washed with brine (500 ml) and dried over sodium sulfate. The solvent was removed in vacuo to afford 175 g (92% of theory) of 1-(2,2,4-trimethyl-cyclohex-3-enyl)-ethanone O-methyl-oxime as a clear red oil.

後処理

  1. customMethanol was removed under reduced pressure
  2. additionthe residue poured in water (600 ml)
  3. addition1N hydrochloric acid was added (100 ml)
  4. extractionThe solution was extracted with dichloromethane (3×300 ml)
  5. washCombined organic layers were washed with brine (500 ml)
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-949bef1b62f54a69bbcb37a365ea0c46
出典データセット
uspto-grants-2013_09
特許番号
US08536215B2

関連ノート

読み込み中…