Lithium borohydride → HCID 58541880, compound

HRID 1966796Notes

Reaction equation

HRID 1966796 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:14][N:13]=[CH:12][CH:11]=1.[BH4-].[Li+]>C1COCC1>[O:14]1[C:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][OH:2])=[CH:11][CH:12]=[N:13]1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 58542033HCID 58542033, compound

Product 1

HCID 58541880HCID 58541880, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-isoxazol-5-yl-benzoic acid methyl ester (385 mg, 1.895 mmol) in THF (4 mL) is added lithium borohydride (82.5 mg, 3.790 mmol). The reaction mixture is stirred at room temperature for 42 hours. After this time, the reaction mixture is quenched with 1N hydrochloric acid aqueous solution and is extracted with EtOAc (2×10 mL). The organics are combined and washed with brine, dried over Na2SO4 (500 mg), filtered and concentrated in vacuo. The residue is purified using silica gel flash column chromatography with 1-10% MeOH in CH2Cl2 as the eluent to give (2-isoxazol-5-yl-phenyl)-methanol (170 mg, 51%).

Workup

  1. customAfter this time, the reaction mixture is quenched with 1N hydrochloric acid aqueous solution
  2. extractionis extracted with EtOAc (2×10 mL)
  3. washwashed with brine
  4. dry with materialdried over Na2SO4 (500 mg)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified

Sources & evidence

ORD record
ord-482204427c5a4e9dba9fb0c6ccbcc01e
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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