Trimethylsilyl cyanide → HCID 22993564, compound

HRID 1275199Notes

Reaction equation

HRID 1275199 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=[O:6].C[Si]([C:15]#[N:16])(C)C.CCCCCC.CCOC(C)=O>CO>[OH:6][CH:5]([C:4]1[CH:7]=[CH:8][C:9]([F:10])=[C:2]([F:1])[CH:3]=1)[C:15]#[N:16]

Participants

5

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 5880883,4-DifluorobenzaldehydeHCID 21226206Ethyl acetate hexane

Product 1

HCID 22993564HCID 22993564, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3,4-difluorobenzaldehyde (2.86 g, 20.0 mmol) in MeOH (20 mL)in a round bottom flask was added trimethylsilyl cyanide (4.0 mL., 30.0 mmol) at 0° C. The reaction mixture was stirred at room temperature for 10 h when TLC analysis indicated that the reaction was complete (Rf =0.4, 3:2 hexane/EtOAc). Solvent was removed in vacuo and hydroxy-(3,4-difluorophenyl)-acetonitrile was obtained as a colorless liquid (crude wt.=3.4 g). It was used in the next step without purification.

Workup

  1. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-44a3e554b8c44f29af92aa83490d444d
Source dataset
uspto-grants-2000_12
Patent number
US06159990

Reaction notes

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