Lithium borohydride → HCID 58541954, compound

HRID 1966716Notes

Reaction equation

HRID 1966716 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[C:11]1[O:15][N:14]=[C:13]([CH3:16])[N:12]=1.[Li+].[BH4-]>C1COCC1>[Cl:10][C:8]1[CH:7]=[CH:6][C:5]([C:11]2[O:15][N:14]=[C:13]([CH3:16])[N:12]=2)=[C:4]([CH2:3][OH:2])[CH:9]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 58541988HCID 58541988, compound

Product 1

HCID 58541954HCID 58541954, compoundYield 9.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of impure 5-chloro-2-(3-methyl-1,2,4-oxadiazol-5-yl)-benzoic acid methyl ester (900 mg) in THF (10.0 mL) is added a solution of 2M LiBH4 in THF (3.6 mL, 7.2 mmol). The reaction mixture is stirred at room temperature for 16 hours and then quenched with 1M HCl aq (50 mL). The quenched reaction mixture is extracted with EtOAc (50 mL×2) 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 35% EtOAc in heptanes as the eluent to afford [5-chloro-2-(3-methyl-1,2,4-oxadiazol-5-yl)-phenyl]-methanol (78 mg) and the regiosiomer [4-chloro-2-(3-methyl-1,2,4-oxadiazol-5-yl)-phenyl]-methanol (60 mg).

Workup

  1. customquenched with 1M HCl aq (50 mL)
  2. customThe quenched reaction mixture
  3. extractionis extracted with EtOAc (50 mL×2)
  4. dry with materialthe combined organic layers are dried with Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated under reduced pressure
  7. customthe residue is purified by silica gel flash column chromatography with 35% EtOAc in heptanes as the eluent

Sources & evidence

ORD record
ord-5c3a0e29596b44fa802237f2f4aa1103
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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