Lithium borohydride → 2-Benzyloxy-4-hydroxymethyl-benzonitrile

HRID 1421743Notes

Reaction equation

HRID 1421743 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][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:5]=1.[Li+].[BH4-]>C1COCC1>[CH2:13]([O:12][C:6]1[CH:5]=[C:4]([CH2:3][OH:2])[CH:9]=[CH:8][C:7]=1[C:10]#[N:11])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 538707413-Benzyloxy-4-cyano-benzoic acid methyl ester

Product 1

HCID 212192292-Benzyloxy-4-hydroxymethyl-benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

3-Benzyloxy-4-cyano-benzoic acid methyl ester from step 1 (400 mg, 1.5 mmol ) was dissolved in THF (7.5 ml). LiBH4 in THF (2 M, 1.5 ml, 3 mmol) was added. The reaction mixture was heated at 70° C. for 3 hours. The reaction 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 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-75910860046a48e48bfcbbd2fda20873
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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