Sodium borohydride → HCID 70977234, compound

HRID 712682Notes

Reaction equation

HRID 712682 reaction equation
C([O:3][C:4](=O)[C:5]([C:8]1[CH:9]=[N:10][CH:11]=[C:12]([Br:14])[CH:13]=1)([CH3:7])[CH3:6])C.[BH4-].[Na+]>CO>[Br:14][C:12]1[CH:13]=[C:8]([C:5]([CH3:7])([CH3:6])[CH2:4][OH:3])[CH:9]=[N:10][CH:11]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 71742853HCID 71742853, compound

Product 1

HCID 70977234HCID 70977234, compoundYield 31.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(5-bromo-pyridin-3-yl)-2-methyl-propionic acid ethyl ester (2.4 g, 0.009 mol) in MeOH (30 mL) is added sodium borohydride (1.7 g, 0.044 mol). The resulting mixture is heated to reflux for 5 h. The reaction is cooled to room temperature and concentrated then is washed with water and extracted with DCM. The combined organic layers are dried (Na2SO4), concentrated and purified by silica gel column to obtain 2-(5-bromo-pyridin-3-yl)-2-methyl-propan-1-ol (661 mg).

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureto reflux for 5 h
  3. concentrationconcentrated
  4. washthen is washed with water
  5. extractionextracted with DCM
  6. dry with materialThe combined organic layers are dried (Na2SO4)
  7. concentrationconcentrated
  8. custompurified by silica gel column

Sources & evidence

ORD record
ord-8a0f6395a8b3403fa4d9a97da94d8ac1
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

Loading…