Lithium borohydride → (2-Chloro-6-methoxypyridin-4-yl)methanol

HRID 1355470Notes

Reaction equation

HRID 1355470 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](OC)=[O:9])[CH:5]=[C:4]([O:12][CH3:13])[N:3]=1.[Li+].[BH4-]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([O:12][CH3:13])[N:3]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 13339618Methyl 2-chloro-6-methoxyisonicotinate

Product 1

HCID 11457961(2-Chloro-6-methoxypyridin-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (2-chloro-6-methoxypyridin-4-yl)carboxylate (15-1, 2.0 g, 9.92 mmole) in dry THF (40 mL) was added LiBH4 (7.4 mL, 2 M in THF, 14.88 mmole) then the mixture was heated to reflux. After 18 hr the mixture was cooled to RT and quenched by slow addition of H2O. The layers were separated and the aqueous layer extracted with EtOAc (2×). The combined organic layers were dried (MgSO4), filtered, and concentrated to give the titled compound a white solid which was sufficiently pure for use in the next step. 1H-NMR (500 MHz, CDCl3) δ6.90 (s, 1H), 6.65 (s, 1H), 4.67 (m, 2H), 3.94 (s, 3H).

Workup

  1. temperaturethe mixture was heated to reflux
  2. customquenched by slow addition of H2O
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with EtOAc (2×)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-efb9e9aa5e8e419a8418883f2989f85f
Source dataset
uspto-grants-2003_07
Patent number
US06586423B2

Reaction notes

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