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

HRID 449248

반응식

HRID 449248 반응식
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

참가 물질

6

반응물 5

HCID 3283Diethyl Ether2회HCID 6328Methyl iodideHCID 736812Methyl quinoline-6-carboxylateHCID 5462224MagnesiumHCID 178418373HCID 178418373, 화합물

생성물 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9e7211fc011d418fa592419e429e4271
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481739B2

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