Ethylene Oxide → 3-Butyn-1-ol, 4-(4-chlorophenyl)-

HRID 1789448Notes

Reaction equation

HRID 1789448 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][CH:3]=1.C([Li])CCC.[CH2:15]1[O:17][CH2:16]1.[Cl-].[NH4+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:15][CH2:16][OH:17])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6354Ethylene OxideHCID 25517Ammonium ChlorideHCID 70118Benzene, 1-chloro-4-ethynyl-HCID 178418339Butyllithium

Product 1

HCID 122603533-Butyn-1-ol, 4-(4-chlorophenyl)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Dissolve 14.2 g (0.104 mole) of 1-chloro-4-ethynylbenzene in 35 ml dry THF and cool to -78° C. Add 49 ml butyl lithium to cold reaction mixture and allow to warm to room temperature for 2 hours. After 2 hours, cool to -78° C. and the add 5.8 ml (0.114 mole) ethylene oxide in 20 ml THF. Allow to warm to room temperature. Monitor progress of reaction with thin-layer chromatography on silica gel (methylene chloride). After 18 hours, add 150 ml saturated aqueous ammonium chloride solution and extract with 150 ml diethyl ether. Wash organic layer with 2×100 ml saturated aqueous sodium chloride solution. Dry organic layer with magnesium sulfate and then filter, and evaporate solvent to obtain the title compound.

Workup

  1. customto cold reaction mixture
  2. temperatureto warm to room temperature for 2 hours
  3. temperaturecool to -78° C.
  4. temperatureto warm to room temperature
  5. customMonitor progress of reaction with thin-layer chromatography on silica gel (methylene chloride)
  6. waitAfter 18 hours
  7. extractionextract with 150 ml diethyl ether
  8. filtrationDry organic layer with magnesium sulfate and then filter
  9. customevaporate solvent

Sources & evidence

ORD record
ord-bdc533e715184965bbc0536d30ee978f
Source dataset
uspto-grants-1987_08
Patent number
US04689341

Reaction notes

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