Lithium borohydride → HCID 18779715, compound

HRID 1585919Notes

Reaction equation

HRID 1585919 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][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[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][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:5]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 53638138HCID 53638138, compound

Product 1

HCID 18779715HCID 18779715, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

3-Benzyloxy-4-cyano-benzoic acid methyl ester from step 1 (84 mg, 0.30 mmol) was dissolved in THF (1.5 ml). LiBH4 in THF (2M, 300 μl, 0.60 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-15837ccbe8e149ce8c5664470bb545d2
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Reaction notes

Loading…