Lithium borohydride → 2-(2,2,2-Trifluoro-ethoxy)-4-hydroxymethyl-benzonitrile

HRID 1585916Notes

Reaction equation

HRID 1585916 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]([F:17])([F:16])[F:15])[CH:5]=1.[Li+].[BH4-]>C1COCC1>[F:15][C:14]([F:16])([F:17])[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]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 543497954-Cyano-3-(2,2,2-trifluoro-ethoxy)-benzoic acid methyl ester

Product 1

HCID 187796882-(2,2,2-Trifluoro-ethoxy)-4-hydroxymethyl-benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

4-Cyano-3-(2,2,2-trifluoro-ethoxy)-benzoic acid methyl ester from step 1 (1.6 g, 6.2 mmol ) was dissolved in THF (62 ml). LiBH4 in THF (2M, 6.2 ml, 12.4 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 (3×10 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-4368df320f96498f90a6aa62ec1d9530
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Reaction notes

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