Diethyl Ether → HCID 57707923, compound

HRID 216898Notes

Reaction equation

HRID 216898 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]([CH:18]=[O:19])=[CH:16][C:15]2[C:10](=[CH:11][C:12]([F:20])=[CH:13][CH:14]=2)[N:9]=1.O1CCC[CH2:22]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:17]([CH:18]([OH:19])[CH3:22])=[CH:16][C:15]2[C:10](=[CH:11][C:12]([F:20])=[CH:13][CH:14]=2)[N:9]=1

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 57707810HCID 57707810, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 57707923HCID 57707923, compound

Procedure

To a stirring mixture of 2-(2-chlorophenyl)-7-fluoroquinoline-3-carbaldehyde (0.7588 g, 2.656 mmol) in tetrahydrofuran (26.56 mL, 2.656 mmol) was added methylmagnesium bromide 3 M in diethyl ether (1.328 mL, 3.984 mmol) dropwise at 0° C. (started at 4:00 μm), and the mixture was allowed to warm to room temperature with stirring over 19 h. The reaction was quenched with saturated aq. NH4Cl (50 mL) and extracted with EtOAc (50 mL×1). The combined organic layers were washed with water (50 mL×1), brine (50 mL×1), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue 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-(2-(2-chlorophenyl)-7-fluoroquinolin-3-yl)ethanol as a yellow syrup: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.63 (1H, d, J=11.0 Hz), 8.20 (1H, dd, J=8.6, 6.7 Hz), 7.75 (1H, dd, J=10.6, 2.7 Hz), 7.42-7.66 (5H, m), 5.39 (1H, dd, J=57.5, 3.9 Hz), 4.59-4.69 (1H, m), 1.20 (3H, dd, J=58.7, 6.3 Hz); LC-MS (ESI) m/z 302.0 [M+H]+.

Workup

  1. customThe reaction was quenched with saturated aq. NH4Cl (50 mL)
  2. extractionextracted with EtOAc (50 mL×1)
  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. customThe residue was purified by silica gel column chromatography on a 80 g of Redi-Sep™ column
  8. customover 25 min

Sources & evidence

ORD record
ord-3ebd84bc80bd4d57b4ffeca2566404ab
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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