Diethyl Ether → 2-(Quinolin-6-yl)propan-2-ol

HRID 449248

反応式

HRID 449248 の反応式
C[Mg]I.[Mg].[CH3:5]I.[N:7]1[C:16]2[C:11](=[CH:12][C:13](C(OC)=O)=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1.C([O:23][CH2:24][CH3:25])C>>[N:7]1[C:16]2[C:11](=[CH:12][C:13]([C:24]([OH:23])([CH3:25])[CH3:5])=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1

参加物

6

反応物 5

HCID 3283Diethyl Ether2 回HCID 6328Methyl iodideHCID 736812Methyl quinoline-6-carboxylateHCID 5462224MagnesiumHCID 178418373HCID 178418373、化合物

生成物 1

HCID 669948782-(Quinolin-6-yl)propan-2-ol収率 84%

実験手順

To an ice-cold solution of methylmagnesium iodide prepared from magnesium (0.454 g, 18.69 mmol) and methyliodide (1.16 ml, 18.69 mmol) in diethyl ether (15 ml), methyl quinoline-6-carboxylate (0.50 g, 2.67 mmol) in diethyl ether (5 ml) was added and warmed to room temperature. After 12 h, the reaction mixture was cooled to 0° C., quenched with dil. 6N HCl and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure and column chromatographed with ethyl acetate: petroleum ether to afford the title compound as a yellow liquid (0.42 g, 84%). 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 8.83 (dd J=4.2, 1.7 Hz, 1H), 8.34 (dd, J=8.2, 1.1 Hz, 1H), 8.00 (d, J=1.9 Hz, 1H), 7.95 (d, J=8.8 Hz, 1H), 7.88 (dd, J=8.9, 2.0 Hz, 1H), 7.50 (q, J=4.1 Hz, 1H), 5.23 (s, 1H), 1.51 (s, 6H).

後処理

  1. additionwas added
  2. temperaturethe reaction mixture was cooled to 0° C.
  3. customquenched with dil. 6N HCl
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. concentrationconcentrated under reduced pressure and column
  7. customchromatographed with ethyl acetate

出典と根拠

ORDレコード
ord-9e7211fc011d418fa592419e429e4271
出典データセット
uspto-grants-2013_07
特許番号
US08481739B2

関連ノート

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