Lithium borohydride → 4-Hydroxymethylbiphenyl-2-carbonitrile

HRID 1585946Notes

Reaction equation

HRID 1585946 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([C:11]#[N:12])[C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)=O.[Li+].[BH4-]>C1COCC1>[OH:2][CH2:3][C:5]1[CH:10]=[C:9]([C:11]#[N:12])[C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 53846446Methyl 2-cyano-4-biphenylcarboxylate

Product 1

HCID 187797454-Hydroxymethylbiphenyl-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

6-Cyano-biphenyl-4-carboxylic acid methyl ester from step 2 (1.4 g, 5.9 mmol) was dissolved in THF (24 ml). LiBH4 in THF (2M, 5.9 ml, 11.8 mmol) was added. The reaction mixture was heated to 70° C. for 3 hours. The reaction mixture 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. FAB MS: 210 m/z (M+ +H)

Workup

  1. customThe reaction mixture 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-0e4efb9bf54e482b9fc04ade46c45265
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Reaction notes

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