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Water → 6-(2-methoxyphenyl)-2,2,4-trimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester

HRID 25781
ノート
印刷プレビュー

反応式

HRID 25781 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([CH3:20])([CH3:19])[CH:13]=[C:12]2[CH3:21].[Li]CCCC.[C:27]([O:31][C:32](=O)[O:33]C(C)(C)C)([CH3:30])([CH3:29])[CH3:28].O>C(Cl)Cl.CCCCCC>[C:27]([O:31][C:32]([N:15]1[C:16]2[C:11](=[CH:10][C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])=[CH:18][CH:17]=2)[C:12]([CH3:21])=[CH:13][C:14]1([CH3:20])[CH3:19])=[O:33])([CH3:30])([CH3:29])[CH3:28]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 225665156-(2-Methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinolineHCID 178418339Butyllithium

生成物 1

HCID 207603346-(2-methoxyphenyl)-2,2,4-trimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester収率 42.9%

試薬・触媒・溶媒 2

HCID 6344
Dichloromethane
溶媒
HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

A mixture of 2.4 g of 6-(2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (see Example 1) in 35 mL of CH2Cl2 was cooled down to −78° C. To this mixture, 13.1 mL of 1.6 M n-BuLi in hexane was added dropwise. The mixture was warmed to 0° C. and 2.9 g of (di-tert-butyl)carbonate was added. The mixture was allowed to stir at 0° C. for 1 hour. The reaction was then worked up by adding water and extracting with EtOAc three times. The organic layers were combined, washed sequentially with 1 N HCl, water, saturated aqueous sodium bicarbonate solution, water, saturated aqueous NaCl solution, dried over magnesium sulfate, and the solvent evaporated in vacuo. The residue was purified by flash chromatography to yield 1.4 g of 6-(2-methoxyphenyl)-2,2,4-trimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester as a solid.

後処理

  1. temperatureThe mixture was warmed to 0° C.
  2. extractionextracting with EtOAc three times
  3. washwashed sequentially with 1 N HCl, water, saturated aqueous sodium bicarbonate solution, water, saturated aqueous NaCl solution
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent evaporated in vacuo
  6. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-1f8bf4aae3f14dbab3f2ec3865b2b222
出典データセット
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06858627B2

反応ノート

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