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

HRID 65226

반응식

HRID 65226 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-01834e72521f43caa6f799cf0744450a
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04613609

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