Ethylene Oxide → HCID 178505502, compound

HRID 26714Notes

Reaction equation

HRID 26714 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[CH:2].C([Mg:18][Br:19])C.[CH2:20]1[O:22][CH2:21]1>C1COCC1>[F:15][C:12]1[CH:13]=[CH:14][C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[C:2][CH2:20][CH2:21][O:22][Mg:18][Br:19])=[CH:4][CH:5]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6354Ethylene OxideHCID 196905164-Ethynyl-4'-fluoro-1,1'-biphenylHCID 178418443HCID 178418443, compound

Product 1

HCID 178505502HCID 178505502, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

19.6 g. of 4-ethynyl-4'-fluorobiphenyl in 200 ml. THF is converted with an excess of ethyl magnesium bromide to the Grignard compound, to which is added 100 ml. of THF and then a solution of 5 g. of ethylene oxide in 10 ml. of THF. After subsidance of the exothermic reaction, the mixture is heated under reflux for 1 hour. 4-(4'-Fluoro-4-biphenylyl)-3-butyn-1-oxymagnesium bromide is thereby formed in situ. To this is added 150 ml. of 1 N hydrochloric acid. After stirring for 20 minutes at 20° and the usual work up, 4-(4'-fluoro-4-biphenylyl)-3-butyn-1-ol, m.p. 134°, is obtained.

Workup

  1. additionto which is added 100 ml
  2. customAfter subsidance of the exothermic reaction
  3. temperaturethe mixture is heated
  4. temperatureunder reflux for 1 hour

Sources & evidence

ORD record
ord-242c5be1cd6e4e03bc6ce430f2e03d00
Source dataset
uspto-grants-1979_04
Patent number
US04151294

Reaction notes

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