Lithium borohydride → HCID 58542045, compound

HRID 1966775Notes

Reaction equation

HRID 1966775 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[C:11]1[N:12]([CH3:16])[N:13]=[CH:14][N:15]=1.[Li+].[BH4-]>C1COCC1>[F:10][C:8]1[CH:7]=[CH:6][C:5]([C:11]2[N:12]([CH3:16])[N:13]=[CH:14][N:15]=2)=[C:4]([CH2:3][OH:2])[CH:9]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 58541909HCID 58541909, compound

Product 1

HCID 58542045HCID 58542045, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 5-fluoro-2-(2-methyl-2H-1,2,4-triazol-3-yl)-benzoic acid methyl ester plus regioisomer (1.5 g, 6.38 mmol) in THF (50.0 mL) is added a solution of 2 M LiBH4 in THF (10.0 mL, 20 mmol). The reaction mixture is stirred at room temperature for 16 hours and is then quenched with 4 M HCl in dioxane to give an acidic solution and concentrated under reduced pressure. The resulting residue is diluted with 1 M aqueous NaOH (100 mL), extracted with EtOAc (10 mL×3) and the combined organic layers are dried with Na2SO4 and filtered. The filtrate is concentrated under reduced pressure and the residue is purified by silica gel flash column chromatography with 6% MeOH in CH2Cl2 as the eluent to afford [5-fluoro-2-(2-methyl-2H-1,2,4-triazol-3-yl)-phenyl]-methanol plus regiosiomer (1.0 g, 75%).

Workup

  1. customis then quenched with 4 M HCl in dioxane
  2. customto give an acidic solution
  3. concentrationconcentrated under reduced pressure
  4. additionThe resulting residue is diluted with 1 M aqueous NaOH (100 mL)
  5. extractionextracted with EtOAc (10 mL×3)
  6. dry with materialthe combined organic layers are dried with Na2SO4
  7. filtrationfiltered
  8. concentrationThe filtrate is concentrated under reduced pressure
  9. customthe residue is purified by silica gel flash column chromatography with 6% MeOH in CH2Cl2 as the eluent

Sources & evidence

ORD record
ord-ecef5ba8b73a432a8ce1bc6d450dd4fb
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

Loading…