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

HRID 1421739Notes

Reaction equation

HRID 1421739 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 (2 M, 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-a648bc5b99324135824d815245a532d2
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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