Diethyl Ether → HCID 57707773, compound

HRID 216895Notes

Reaction equation

HRID 216895 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([CH:22]=[O:23])=[N:10][C:11]2[C:16]([N:17]=1)=[C:15]([C:18]([F:21])([F:20])[F:19])[CH:14]=[CH:13][CH:12]=2.O1CCC[CH2:25]1.C[Mg]Br.C(OCC)C>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([CH:22]([OH:23])[CH3:25])=[N:10][C:11]2[C:16]([N:17]=1)=[C:15]([C:18]([F:19])([F:20])[F:21])[CH:14]=[CH:13][CH:12]=2

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 57707780HCID 57707780, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 57707773HCID 57707773, compound

Procedure

To a stirring heterogeneous mixture of 3-(2-chlorophenyl)-5-(trifluoromethyl)-quinoxaline-2-carbaldehyde (0.2129 g, 0.632 mmol) in tetrahydrofuran (6.32 mL, 0.632 mmol) was added methylmagnesium bromide 3 M in diethyl ether (0.632 mL, 1.90 mmol) dropwise at 0° C. (started at 11:20 am), and the mixture was then stirred at room temperature. After 3 h, the reaction was quenched with saturated aq. NH4Cl (50 mL) and extracted with EtOAc (50 mL×2). The combined organic layers were washed with water (50 mL×1), brine (50 mL×1), dried over Na2SO4, filtered, and concentrated under reduced pressure to give a brown syrup. The brown syrup was purified by silica gel column chromatography on a 80 g of Redi-Sep™ column using 0 to 50% gradient of EtOAc in hexane over 25 min and then 50% isocratic of EtOAc for 10 min as eluent to give 1-(3-(2-chlorophenyl)-5-(trifluoromethyl)quinoxalin-2-yl)ethanol as a solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.47 (1H, d, J=8.6 Hz), 8.31 (1H, d, J=7.0 Hz), 8.05 (1H, t, J=8.0 Hz), 7.48-7.71 (4H, m), 5.33 (1H, br. s.), 4.84 (1H, br. s.), 1.28-1.55 (3H, m); LC-MS (ESI) m/z 353.0 [M+H]+.

Workup

  1. customthe reaction was quenched with saturated aq. NH4Cl (50 mL)
  2. extractionextracted with EtOAc (50 mL×2)
  3. washThe combined organic layers were washed with water (50 mL×1), brine (50 mL×1)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a brown syrup
  8. customThe brown syrup was purified by silica gel column chromatography on a 80 g of Redi-Sep™ column
  9. customover 25 min

Sources & evidence

ORD record
ord-6859d636c5ae4038a0f511e1ce0abada
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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