Lithium borohydride → HCID 18779681, compound

HRID 1421762Notes

Reaction equation

HRID 1421762 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[C:6]([C:12]#[N:13])[CH:5]=1.[Li+].[BH4-]>C1COCC1>[OH:2][CH2:3][C:4]1[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:8][CH:9]=1)[C:10]#[N:11]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 14495336HCID 14495336, compound

Product 1

HCID 18779681HCID 18779681, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

3,4-Dicyano-benzoic acid methyl ester from step 1 (2.4 g, 12.9 mmol ) was dissolved in THF (65 ml). LiBH4 in THF (2 M, 12.9 ml, 25.8 mmol) was added. The reaction mixture was heated to 70° C. for 3 hours. The reaction was quenched carefully with 3N HCl and then extracted with EtOAc (3×20 mL). The organic layers were combined, washed with brine, dried (MgSO4), filtered and concentrated to yield the desired product.

Workup

  1. customThe reaction was quenched carefully with 3N HCl
  2. extractionextracted with EtOAc (3×20 mL)
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d0684c9bc57c46819bd5b608c81902ac
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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