Lithium borohydride → HCID 22016838, compound

HRID 1421755Notes

Reaction equation

HRID 1421755 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[C:6]([O:12][CH3:13])[CH:5]=1.[Li+].[BH4-]>C1COCC1>[OH:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[C:6]([O:12][CH3:13])[CH:5]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 22464400Methyl 4-cyano-3-methoxybenzoate

Product 1

HCID 22016838HCID 22016838, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

4-Cyano-3-methoxy-benzoic acid methyl ester from step 1 (4.7 g, 25 mmol) was dissolved in THF (125 ml). LiBH4 in THF (2 M, 25 ml, 50 mmol) was added. The reaction mixture was heated at 70° C. for 3 hours. The reaction mixture was quenched carefully with 3N HCl and then extracted with EtOAc (3×10 mL). The organic layers were combined, washed with brine, dried (MgSO4), filtered and concentrated to yield the desired product.

Workup

  1. customThe reaction mixture was quenched carefully with 3N HCl
  2. extractionextracted with EtOAc (3×10 mL)
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9d7ab8b025c7401dac8bcbaf11c7aaac
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

Loading…