Trimethylsilyldiazomethane → HCID 53710760, compound

HRID 631542Notes

Reaction equation

HRID 631542 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[F:8][C:9]([F:16])([F:15])[C:10](=[O:14])[CH2:11][C:12]#[N:13]>C(OCC)C>[F:8][C:9]([F:16])([F:15])[C:10]([O:14][CH3:1])=[CH:11][C:12]#[N:13]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 138435404,4,4-Trifluoro-3-oxobutanenitrile

Product 1

HCID 53710760HCID 53710760, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

(Trimethylsilyl)diazomethane (21 mL, 2M in diethyl ether) was added dropwise to a solution of 4,4,4-trifluoro-3-oxobutanenitrile (3.79 g, 26 mmol) in anhydrous diethyl ether (25 mL) previously cooled to 0° C. The resulting mixture was allowed to slowly warm to room temperatureand stirred overnight. The solvent was removed under reduced pressure to give 4,4,4-trifluoro-3-methoxybut-2-enenitrile, which was directly used in the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 5.00 (s, 1H), 4.16 (s, 3H).

Workup

  1. temperatureto slowly warm to room temperatureand
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-31ffe4a07ccd42608be484e6a320e837
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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