Ethyl 5-bromopyridine-3-carboxylate → (5-Bromo-3-pyridinyl)methanol

HRID 2244204Notes

Reaction equation

HRID 2244204 reaction equation
[BH4-].[Na+].C([O:5][C:6](=O)[C:7]1[CH:12]=[C:11]([Br:13])[CH:10]=[N:9][CH:8]=1)C>C(O)C>[Br:13][C:11]1[CH:12]=[C:7]([CH2:6][OH:5])[CH:8]=[N:9][CH:10]=1

Participants

4

Reactant 2

HCID 140785Ethyl 5-bromopyridine-3-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 2784733(5-Bromo-3-pyridinyl)methanolYield 34.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Crushed pellets of sodium borohydride were added over 30 minutes to a solution of 5-bromonicotinic acid ethyl ester of Step A (5.0 g, 21.7 mmol) in ethanol (150 mL). The reaction was stirred at room temperature for five days and then quenched with water. The ethanol was removed under reduced pressure and the aqueous residue was extracted three times with methylene chloride. The combined organics were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to a yellow oil. The material was purified by flash chromatography over silica gel Marck-60 using 2:1 hexane/ethyl acetate as an eluant to give the title compound (1.41 g) as a light yellow liquid which was used in the next step without further purification.

Workup

  1. customquenched with water
  2. customThe ethanol was removed under reduced pressure
  3. extractionthe aqueous residue was extracted three times with methylene chloride
  4. dry with materialThe combined organics were dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure to a yellow oil
  6. customThe material was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-5ea50f64b21c440493305b6f6376e33e
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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