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

HRID 1404767Notes

Reaction equation

HRID 1404767 reaction equation
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

Participants

6

Reactant 5

HCID 3283Diethyl Ether2×HCID 6328Methyl iodideHCID 736812Methyl quinoline-6-carboxylateHCID 5462224MagnesiumHCID 178418373HCID 178418373, compound

Product 1

HCID 669948782-(Quinolin-6-yl)propan-2-ol

Procedure

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 brown oil (0.41 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).

Workup

  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

Sources & evidence

ORD record
ord-d86c254f7fd84440908db561db4eda7f
Source dataset
uspto-grants-2014_12
Patent number
US08912331B2

Reaction notes

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