Sodium borohydride → HCID 21660613, compound

HRID 594235Notes

Reaction equation

HRID 594235 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[N:11]=[C:10]([C:12](OC)=[O:13])[CH:9]=[CH:8][CH:7]=1.[BH4-].[Na+]>CCO>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[N:11]=[C:10]([CH2:12][OH:13])[CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69084075HCID 69084075, compound

Product 1

HCID 21660613HCID 21660613, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 6-(thiazol-2-yl)picolinate (230 mg; 1.04 mmol) in anh. EtOH (3 ml) was treated with NaBH4 (197 mg; 5.22 mmol), and the resulting mixture was stirred at rt, under nitrogen, for 17 h. After concentration to dryness under reduced pressure, the resulting residue was treated with water, and extracted with DCM. The organic layer was then dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=25/1) afforded (6-(thiazol-2-yl)pyridin-2-yl)methanol as an orange solid. LC-MS (conditions A): tR=0.45 min.; [M+H]+: 193.05 g/mol.

Workup

  1. concentrationAfter concentration to dryness under reduced pressure
  2. additionthe resulting residue was treated with water
  3. extractionextracted with DCM
  4. dry with materialThe organic layer was then dried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customPurification by FC (DCM/MeOH=25/1)

Sources & evidence

ORD record
ord-9f2965db760f476aa85d4bfd83d1c236
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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