Tetrahydrofuran → (2-(3-Fluorophenyl)-8-methoxyquinolin-3-yl)methanol

HRID 216855Notes

Reaction equation

HRID 216855 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]([CH:18]=[O:19])=[CH:16][C:15]3[C:10](=[C:11]([O:20][CH3:21])[CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.O1CCCC1.[BH4-].[Na+]>>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]([CH2:18][OH:19])=[CH:16][C:15]3[C:10](=[C:11]([O:20][CH3:21])[CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 577080272-(3-Fluorophenyl)-8-methoxyquinoline-3-carbaldehyde

Product 1

HCID 68945460(2-(3-Fluorophenyl)-8-methoxyquinolin-3-yl)methanol

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(3-fluorophenyl)-8-methoxyquinoline-3-carbaldehyde (2.2967 g, 8.165 mmol) in tetrahydrofuran (40.83 mL, 8.165 mmol) at 0° C. was added sodium borohydride (0.4634 g, 12.25 mmol) and the mixture was stirred at 0° C. After 1 h of stirring at 0° C., the mixture was partitioned between EtOAc (100 mL) and H2O (100 mL), and the organic layer was washed with brine (100 mL×2), dried over Na2SO4, filtered, and concentrated under reduced pressure to give (2-(3-fluorophenyl)-8-methoxyquinolin-3-yl)methanol as a brown solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.43 (1H, s), 7.46-7.60 (5H, m), 7.29-7.36 (1H, m), 7.19 (1H, dd, J=7.4, 1.6 Hz), 5.50 (1H, t, J=5.3 Hz), 4.61 (2H, dd, J=5.5, 0.8 Hz), 3.96 (3H, s); LC-MS (ESI) m/z 284.0 [M+H]+. The brown solid was carried on crude without purification for the next step.

Workup

  1. stirringAfter 1 h of stirring at 0° C.
  2. customthe mixture was partitioned between EtOAc (100 mL) and H2O (100 mL)
  3. washthe organic layer was washed with brine (100 mL×2)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-00ac95fc30044e66b969e583cb280995
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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