Tetrahydrofuran → HCID 57707874, compound

HRID 1397757Notes

Reaction equation

HRID 1397757 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][C:19]([F:22])([F:21])[F:20])[C:8]([CH:23]=[O:24])=[CH:7]2.O1CCCC1.[BH4-].[Na+]>>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][C:19]([F:20])([F:21])[F:22])[C:8]([CH2:23][OH:24])=[CH:7]2

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 57707760HCID 57707760, compound

Product 1

HCID 57707874HCID 57707874, compound

Conditions

Temperature
0 °C

Procedure

To a solution of 8-chloro-2-(2-(trifluoromethoxy)phenyl)quinoline-3-carbaldehyde (0.5427 g, 1.543 mmol) in tetrahydrofuran (7.715 mL, 1.543 mmol) at 0° C. was added SODIUM BOROHYDRIDE (0.08757 g, 2.315 mmol) and the mixture was stirred at 0° C. and allowed to warm to room temperature over 1 hour. 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 (50 mL×2), dried over Na2SO4, filtered, and concentrated under reduced pressure to give (8-chloro-2-(2-(trifluoromethoxy)phenyl)quinolin-3-yl)methanol as a light-yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.58 (1 H, s), 8.10 (1 H, dd, J=8.3, 1.3 Hz), 7.95 (1 H, dd, J=7.5, 1.3 Hz), 7.51-7.72 (5 H, m), 5.54 (1 H, s), 4.44 (2 H, s); LC-MS (ESI) m/z 354.0 [M+H]+. The product was carried on crude without purification for the next step.

Workup

  1. temperatureto warm to room temperature over 1 hour
  2. stirringAfter 1 h of stirring at 0° C.
  3. customthe mixture was partitioned between EtOAc (100 mL) and H2O (100 mL)
  4. washthe organic layer was washed with brine (50 mL×2)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-438e6b43943844aab28b59c013fda5ad
Source dataset
uspto-grants-2014_12
Patent number
US08901135B2

Reaction notes

Loading…