Lithium borohydride → 4-Hydroxymethylbiphenyl-2-carbonitrile

HRID 1421773Notes

Reaction equation

HRID 1421773 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 (2 M, 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.

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-0bcc24e365d746aeac2b7c0ccccf4e0b
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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