4-Phenyl-3-butyn-2-one → HCID 178467506, compound

HRID 1604999Notes

Reaction equation

HRID 1604999 reaction equation
[C:1]([C:4]#[C:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:3])[CH3:2].C[Si]([N:16]=[N+:17]=[N-:18])(C)C>CCOCC>[C:1]([C:4]1[N:16]=[N:17][NH:18][C:5]=1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 745554-Phenyl-3-butyn-2-oneHCID 78378Azidotrimethylsilane

Product 1

HCID 178467506HCID 178467506, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 30 g (0.21 mole) of acetylphenyl-acetylene and 24 g (0.21 mole) of trimethylsilyl azide was heated at 140°C for 24 hours. It was then cooled, dissolved in ether, and extracted with dilute sodium hydroxide. This aqueous layer was separated and made acidic with dilute HCl. The precipitate was recrystallized from benzene-petroleum ether to give 11 g (28%) of 4-acetyl-5-phenyltriazole, m.p. 117°-118°C.

Workup

  1. temperatureIt was then cooled
  2. extractionextracted with dilute sodium hydroxide
  3. customThis aqueous layer was separated
  4. customThe precipitate was recrystallized from benzene-petroleum ether

Sources & evidence

ORD record
ord-ee6cfb789d03425da5e8f2cc48fcd23f
Source dataset
uspto-grants-1976_04
Patent number
US03948930

Reaction notes

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