Ethylene Glycol → 2-(3-(3-Methoxyphenyl)-3-(2-methylphenyl)-2-propen-1-yloxy)ethanol

HRID 1614819Notes

Reaction equation

HRID 1614819 reaction equation
C([Li])CCC.[CH2:6]([OH:9])[CH2:7][OH:8].Br[CH2:11][CH:12]=[C:13]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20]>C1(C)C=CC=CC=1>[CH3:28][O:27][C:23]1[CH:22]=[C:21]([C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])=[CH:12][CH2:11][O:8][CH2:7][CH2:6][OH:9])[CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 537403713-Bromo-1-(3-methoxyphenyl)-1-(2-methylphenyl)-1-propeneHCID 178418339Butyllithium

Product 1

HCID 536756102-(3-(3-Methoxyphenyl)-3-(2-methylphenyl)-2-propen-1-yloxy)ethanolYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of n-butyllithium in hexanes (32.2 ml, 2.5 M) was added dropwise under a nitrogen atmosphere to ethylene glycol (60 ml) at 10° C. When addition was complete the mixture was stirred for 0.5 h at room temperature. A solution of 3-bromo-1-(3-methoxyphenyl)-1-(2-methylphenyl)-1-propene (24.4 g, 77 mmol) in toluene (50 ml) was added and the reaction mixture was stirred at room temperature for 4 days and at 65° C. for 6 h. The solvent was evaporated in vacuo, water (250 ml) was added and the mixture was extracted with ethyl acetate (2×200+100 ml). The combined organic phases was dried over magnesium sulphate and the solvent was evaporated in vacuo. Flash chromatography of the residue on silica gel (320 g) using a mixture of cyclohexane and ethyl acetate gradient as eluent provided 16.6 g (72%) of 2-(3-(3-methoxyphenyl)-3-(2-methylphenyl)-2-propen-1-yloxy)ethanol.

Workup

  1. additionWhen addition
  2. stirringthe reaction mixture was stirred at room temperature for 4 days and at 65° C. for 6 h
  3. customThe solvent was evaporated in vacuo, water (250 ml)
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate (2×200+100 ml)
  6. dry with materialThe combined organic phases was dried over magnesium sulphate
  7. customthe solvent was evaporated in vacuo
  8. additiona mixture of cyclohexane and ethyl acetate gradient as eluent

Sources & evidence

ORD record
ord-3d87c7e6df9647dc804611fc7ab38f7a
Source dataset
uspto-grants-1993_03
Patent number
US05198451

Reaction notes

Loading…