Lithium borohydride → HCID 59460759, compound

HRID 2404352Notes

Reaction equation

HRID 2404352 reaction equation
[BH4-].[Li+].[C:3]([C:5]1[CH:14]=[CH:13][C:8]([C:9](OC)=[O:10])=[CH:7][C:6]=1[CH3:15])#[N:4]>C1COCC1.O>[OH:10][CH2:9][C:8]1[CH:13]=[CH:14][C:5]([C:3]#[N:4])=[C:6]([CH3:15])[CH:7]=1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 19969932Methyl 4-cyano-3-methylbenzoate

Product 1

HCID 59460759HCID 59460759, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium borohydride (33 mg, 1.54 mmol) was added into a solution of methyl 4-cyano-3-methylbenzoate (245 mg, 1.40 mmol) in THF (3 mL) and the resulting mixture was stirred at RT for 4 hours. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc (4×20 mL). The combined organic fractions were dried (MgSO4) and concentrated under vacuum. The residue was purified by flash chromatography (silica, petrol ether/EtOAc) to give the title compound as a colorless gum (195 mg, 95%). 1H NMR (CDCl3, 400 MHz) δ 7.58 (1H, d, J=7.9 Hz), 7.33 (1H, s), 7.26 (1H, m), 4.74 (2H, s), 2.55 (3H, s), 1.95 (1H, s). LC/MS (Method A): 144 (M+H)+. HPLC (Method F) Rt 3.95 min (Purity: 95.3%).

Workup

  1. extractionextracted with EtOAc (4×20 mL)
  2. dry with materialThe combined organic fractions were dried (MgSO4)
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by flash chromatography (silica, petrol ether/EtOAc)

Sources & evidence

ORD record
ord-2fce4bf4cf3d49568cb502dc5e99db96
Source dataset
uspto-grants-2014_08
Patent number
US08802704B2

Reaction notes

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