Ethyl chloronicotinate → (2-Chloropyridin-3-yl)methanol

HRID 1046375Notes

Reaction equation

HRID 1046375 reaction equation
[Cl:1][C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4](OCC)=[O:5].[BH4-].[Na+]>CCO>[Cl:1][C:2]1[C:3]([CH2:4][OH:5])=[CH:9][CH:10]=[CH:11][N:12]=1

Participants

4

Reactant 2

HCID 2796614Ethyl chloronicotinateHCID 4311764Sodium borohydride

Product 1

HCID 2763647(2-Chloropyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-chloronicotinate (1 g, 5.39 mmol) in 10 ml EtOH at room temperature is added 2.04 g (53.9 mmol) NaBH4 over 30 minutes in several portions. The solution is stirred for. The excess borohydride is quenched by the addition of methanol. The solvents are evaporated and the residue partitioned between dichloromethane and water. The aqueous Phase is extracted 3× with 10 ml of dichloromethane. The combined organic layers are washed with brine, dried with MgSO4, filtered and evaporated in vacuo to yield a light yellow oil.

Workup

  1. customThe excess borohydride is quenched by the addition of methanol
  2. customThe solvents are evaporated
  3. customthe residue partitioned between dichloromethane and water
  4. extractionThe aqueous Phase is extracted 3× with 10 ml of dichloromethane
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customto yield a light yellow oil

Sources & evidence

ORD record
ord-3803703bb05b4aea91420801ee638026
Source dataset
uspto-grants-2013_10
Patent number
US08569317B2

Reaction notes

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