Ethylene Glycol → HCID 19974710, compound
Reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[CH2:5]([Li])[CH2:6][CH2:7][CH3:8].[CH3:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[Br-].[CH2:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>>[C:12]1(/[C:7](=[CH:6]/[C:5]2[CH:21]=[CH:22][CH:17]=[CH:18][CH:19]=2)/[CH2:8][O:3][CH2:2][CH2:1][OH:4])[CH:11]=[CH:10][CH:15]=[CH:14][CH:13]=1.[C:12]1(/[C:6](=[CH:5]\[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)/[CH2:7][O:3][CH2:2][CH2:1][OH:4])[CH:11]=[CH:10][CH:15]=[CH:14][CH:13]=1Participants
Procedure
Ethylene glycol (40 ml) under an inert atmosphere was cooled on an icebath and a 2.5M solution of n-butyllithium in hexane (23 ml, 58 mmol) was carefully added. After stirring for 20 min at room temperature the above bromide dissolved in a small portion of cyclohexane was added. After removing the hexanes by passing nitrogen over the reaction mixture stirring was continued for 5 h. Water (75 ml) was added and the mixture was extracted with ethyl acetate (3×75 ml). The combined organic phases were washed with water (25 ml) and dried (Na2SO4). The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel (300 g, n-heptane/ethyl acetate=7/3) to give 6.2 g of Z-2-((2,3-diphenyl-2-propen-1-yl)oxy)ethanol and 2.7 g of E-2-((2,3-diphenyl-2-propen-1-yl)oxy)ethanol.
Workup
- additionwas added
- customAfter removing the hexanes
- additionWater (75 ml) was added
- extractionthe mixture was extracted with ethyl acetate (3×75 ml)
- washThe combined organic phases were washed with water (25 ml)
- dry with materialdried (Na2SO4)
- customThe solvent was evaporated in vacuo
- customthe residue was purified by column chromatography on silica gel (300 g, n-heptane/ethyl acetate=7/3)
Sources & evidence
- ORD record
- ord-9efbedc64e934406b8519d8ca56c112b
- Source dataset
- uspto-grants-1997_02
- Patent number
- US05604242
Reaction notes
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