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

HRID 65226

反応式

HRID 65226 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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 then 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.

後処理

  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

出典と根拠

ORDレコード
ord-01834e72521f43caa6f799cf0744450a
出典データセット
uspto-grants-1986_09
特許番号
US04613609

関連ノート

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