Hydrochloric Acid → [4-(5-Ethoxy-2-fluoro-phenyl)-3,6-dimethyl-2-pyridyl]methanol

HRID 2207666Notes

Reaction equation

HRID 2207666 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([F:23])=[C:8]([C:10]2[CH:15]=[C:14]([CH3:16])[N:13]=[C:12]([C:17](OCC)=[O:18])[C:11]=2[CH3:22])[CH:9]=1)[CH3:2].[BH4-].[Na+].Cl>C(O)C>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([F:23])=[C:8]([C:10]2[CH:15]=[C:14]([CH3:16])[N:13]=[C:12]([CH2:17][OH:18])[C:11]=2[CH3:22])[CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 89649447Ethyl 4-(5-ethoxy-2-fluoro-phenyl)-3,6-dimethyl-pyridine-2-carboxylate

Product 1

HCID 89648949[4-(5-Ethoxy-2-fluoro-phenyl)-3,6-dimethyl-2-pyridyl]methanolYield 90.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of ethyl 4-(5-ethoxy-2-fluoro-phenyl)-3,6-dimethyl-pyridine-2-carboxylate (which may be prepared as described in Description 139) (5.51 g, 17.36 mmol) in absolute ethanol (45 mL) under nitrogen at 25° C., was added sodium borohydride (3.28 g, 86.81 mmol) in portions over 40 min. The resulting mixture was left to stir for another 3 h. It was treated with crushed ice (80 mL) and the pH was carefully adjusted to 7 with the addition of 2M HCl. The reaction mixture was extracted with DCM and the organic layers were washed with brine then collected by passing down a PhaseSep cartridge. Evaporation of the volatiles gave [4-(5-ethoxy-2-fluoro-phenyl)-3,6-dimethyl-2-pyridyl]-methanol (D140) (4.33 g, 15.727 mmol, 90.6% yield) as colourless oil;

Workup

  1. waitThe resulting mixture was left
  2. extractionThe reaction mixture was extracted with DCM
  3. washthe organic layers were washed with brine
  4. customthen collected
  5. customEvaporation of the volatiles

Sources & evidence

ORD record
ord-03180d650f964f838c48fa6e9c953e0c
Source dataset
uspto-grants-2016_06
Patent number
US09376436B2

Reaction notes

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