Methyl (E)-3-(2-quinolinyl)-2-propenoate → 3-(Quinolin-2-yl)propan-1-ol

HRID 1626367Notes

Reaction equation

HRID 1626367 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1/[CH:11]=[CH:12]/[C:13](OC)=[O:14].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][CH2:13][OH:14]

Participants

4

Reactant 2

HCID 6479253Methyl (E)-3-(2-quinolinyl)-2-propenoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 218061343-(Quinolin-2-yl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Methyl(2E)-3-(quinolin-2-yl)prop-2-enoate G5 (2.37 g, 11.1 mmol) dissolved in 100 mL THF was cooled to 0° C. and treated with a 1M solution of LAH in THF (33.3 mL, 33.3 mmol) dropwise over 5 minutes. The reaction was allowed to warm to room temperature and stir overnight. The reaction was then carefully quenched with 1.3 mL of water, 1.3 mL of 15% NaOH, and 3.9 mL of water, Solid Na2SO4 was added and the slurry was stirred for 2 hours, filtered and concentrated by rotary evaporation. The residue was purified by silica gel flash column chromatography (EtOAc/hexanes gradient) to provide 575 mg (27%) of G6 as a brown oil. MS (Electrospray): m/z 188.2 (MH+).

Workup

  1. temperatureto warm to room temperature
  2. customThe reaction was then carefully quenched with 1.3 mL of water, 1.3 mL of 15% NaOH, and 3.9 mL of water, Solid Na2SO4
  3. additionwas added
  4. stirringthe slurry was stirred for 2 hours
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation
  7. customThe residue was purified by silica gel flash column chromatography (EtOAc/hexanes gradient)
  8. customto provide 575 mg (27%) of G6 as a brown oil

Sources & evidence

ORD record
ord-1ff5d4c333b74d28aa86e3a6c21b44f0
Source dataset
uspto-grants-2014_07
Patent number
US08785467B2

Reaction notes

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