Ethylene Glycol → HCID 54282101, compound

HRID 1614799Notes

Reaction equation

HRID 1614799 reaction equation
C([Li])CCC.[CH2:6]([OH:9])[CH2:7][OH:8].Br[CH2:11][CH:12]=[C:13]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1>O>[C:24]1([C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[CH:15]=2)=[CH:12][CH2:11][O:8][CH2:7][CH2:6][OH:9])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 53933997HCID 53933997, compoundHCID 178418339Butyllithium

Product 1

HCID 54282101HCID 54282101, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of n-butyllithium in hexanes (16 ml, 2.5 M) was added dropwise under a nitrogen atmosphere to dry ethylene glycol (40 ml) at 10° C. When addition was complete the mixture was stirred for 0.5 h at room temperature. 3-Bromo-1-phenyl-1-(3-(trifluoromethyl)phenyl)-1-propene (12.0 g, 35 mmol, prepared similarly to the method described in Example 23) was added and the reaction mixture was stirred at room temperature for 72 h. The mixture was poured into water (300 ml) and extracted with ethyl acetate (2×100 ml). The combined organic extracts was dried over sodium sulphate and the solvent evaporated in vacuo. Flash chromatography of the residue on silica gel (150 g) using a mixture of cyclohexane and ethyl acetate (7:3) as eluent provided 5.9 g (52%) of 2-(3-phenyl-3-(3-(trifluoromethyl)phenyl)-2-propen-1-yloxy)ethanol. 2-(3-phenyl-3-(3-(trifluoromethyl)phenyl)-2-propen-1-yloxy) ethanol (5.0 g, 15.5 mmol) was dissolved into dry dioxan (80 ml) and stirred under an atmosphere of hydrogen for 18 h at room temperature in the presence of 10% palladium on carbon catalyst (50% aqueous paste) and then filtered. The filtrate was evaporated in vacuo to give 4.0 g (95%) of 2-(3-phenyl-3-(3-trifluoromethyl)phenyl)-1-propyloxy)ethanol. 1H NMR (CDCl3)δ 4.20 (t, 1H).

Workup

  1. additionWhen addition
  2. additionwas added
  3. stirringthe reaction mixture was stirred at room temperature for 72 h
  4. extractionextracted with ethyl acetate (2×100 ml)
  5. dry with materialThe combined organic extracts was dried over sodium sulphate
  6. customthe solvent evaporated in vacuo
  7. additiona mixture of cyclohexane and ethyl acetate (7:3) as eluent

Sources & evidence

ORD record
ord-4e00a6f501a149d3aac1ec4b5b81383b
Source dataset
uspto-grants-1993_03
Patent number
US05198451

Reaction notes

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