Diethyl Ether → 5-(alpha-Hydroxyundecyl)-3-phenylbenzofuran
Reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:6]=2[CH:16]=1.[Mg].[Cl-].[NH4+].C([O:22][CH2:23][CH3:24])C>O1CCCC1.O>[OH:22][CH:23]([C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:6]=2[CH:16]=1)[CH2:24][CH2:4][CH2:3][CH2:2][CH2:16][CH2:6][CH2:7][CH2:10][CH2:11][CH3:12]Participants
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 5.5 g. (0.02 mole) of 5-bromo-3-phenylbenzofuran in tetrahydrofuran is added 0.5 g. (0.02 mole) of magnesium, and the mixture is heated at its reflux temperature for three hours. After cooling to 0° C., 3.4 g. of undecyl aldehyde is added. After stirring for 30 minutes at room temperature, the solution is added to ammonium chloride solution. Evaporation provides a residue which is mixed with diethyl ether and water. The ether layer is separated, washed with saturated sodium chloride solution, dried and evaporated. The resulting oil is dissolved in carbon tetrachloride and eluted from a silica gel column with carbon tetrachloride, then with dichloromethane. The later fractions are evaporated to provide 5-(α-hydroxyundecyl)-3-phenylbenzofuran which is dissolved in dichloromethane.
Workup
- temperaturereflux temperature for three hours
- customEvaporation
- customprovides a residue which
- customThe ether layer is separated
- washwashed with saturated sodium chloride solution
- customdried
- customevaporated
- dissolutionThe resulting oil is dissolved in carbon tetrachloride
- washeluted from a silica gel column with carbon tetrachloride
- customThe later fractions are evaporated
Sources & evidence
- ORD record
- ord-c49d250a9e154af5b535095b9dcf3100
- Source dataset
- uspto-grants-1979_05
- Patent number
- US04153716
Reaction notes
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