Epichlorohydrin → 2-[2-(2-Benzyloxyethoxy)ethoxy]-1-[2-(2-benzyloxyethoxy)ethoxymethyl]ethanol

HRID 1162958노트

반응식

HRID 1162958 반응식
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH2:6]([O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][OH:19])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:20]([CH:22]1[O:24][CH2:23]1)Cl.[Cl-].[NH4+]>C1COCC1>[CH2:1]([O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:23][CH:22]([CH2:20][O:19][CH2:18][CH2:17][O:16][CH2:15][CH2:14][O:13][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[OH:24])[C:2]1[CH:8]=[CH:7][CH:6]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 7835EpichlorohydrinHCID 25517Ammonium ChlorideHCID 2297222-[2-(Benzyloxy)ethoxy]ethan-1-olHCID 178418339Butyllithium

생성물 1

HCID 575581112-[2-(2-Benzyloxyethoxy)ethoxy]-1-[2-(2-benzyloxyethoxy)ethoxymethyl]ethanol수율 23%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of n-butyl lithium in THF (1.6 N, 1.59 mL, 2.55 mmol) was added to 10 mL of a solution of diethylene glycol monobenzyl ether (500 mg, 2.55 mmol) in THF at −78° C., and the mixture was stirred for 15 minutes. Then, DL-epichlorohydrin (0.1 mL, 1.28 mmol) was added thereto. The mixture was stirred at room temperature for one hour and under reflux for one hour. Next, the THF solvent was evaporated under reduced pressure, and the residue was stirred at 100° C. without a solvent to complete the reaction. Aqueous saturated ammonium chloride was added to the residue, followed by extraction with ethyl acetate. The extract was washed with saturated saline and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative liquid chromatography (water:acetonitrile=1:1, 0.05% TFA) to obtain 2-[2-(2-benzyloxyethoxy)ethoxy]-1-[2-(2-benzyloxyethoxy)ethoxymethyl]ethanol (129 mg, yield: 23%) as a colorless oil.

후처리

  1. stirringThe mixture was stirred at room temperature for one hour
  2. temperatureunder reflux for one hour
  3. customNext, the THF solvent was evaporated under reduced pressure
  4. stirringthe residue was stirred at 100° C. without a solvent
  5. customthe reaction
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe extract was washed with saturated saline
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe resulting residue was purified by preparative liquid chromatography (water:acetonitrile=1:1, 0.05% TFA)

출처 및 근거

ORD 기록
ord-8494631fa1374ad9af3c1c5fea5fca59
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820693B2

반응 노트

불러오는 중…