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

HRID 1162958Notes

Reaction equation

HRID 1162958 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-8494631fa1374ad9af3c1c5fea5fca59
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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