Hexane → HCID 69205838, compound
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH2:11][CH3:12])[CH:3]=1.C([Li])CCC.CCCCCC.[N:24]1([C:29]2[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=2)[CH:32]=[O:33])[CH:28]=[CH:27][CH:26]=[CH:25]1>C1COCC1.O>[CH2:11]([O:10][C:4]1[CH:3]=[C:2]([CH:32]([C:31]2[CH:34]=[CH:35][CH:36]=[C:29]([N:24]3[CH:28]=[CH:27][CH:26]=[CH:25]3)[CH:30]=2)[OH:33])[CH:7]=[CH:6][C:5]=1[O:8][CH3:9])[CH3:12]Participants
Procedure
To a solution of 4-bromo-2-ethoxy-1-methoxy-benzene (1.5 g, 6.5 mmol) in THF (30 mL) was added a solution of n-butyllitium in hexane (2.4 mL, 2.5 N, 6.0 mmol) at −78° C. and kept for 20 min. To the mixture was added 3-pyrrol-1-yl-benzaldehyde (1.0 g, 5.8 mmol) at −78° C. After 18 h, water (30 mL) was added to the mixture, and the cold bath was removed. The mixture was stirred at room temperature for 20 min. The mixture was extracted with ethyl acetate (2×50 mL). The combined organic layers was washed with HCl (0.5 N, 50 mL), sodium hydrogen carbonate (50 mL, sat), brine (50 mL) and dried over magnesium sulfate. Removal of solvent gave (3-ethoxy-4-methoxy-phenyl)-(3-pyrrol-1-yl-phenyl)-methanol (1.9 g, 100% crude yield). The sample was used in the next step without further purification.
Workup
- waitAfter 18 h
- customthe cold bath was removed
- extractionThe mixture was extracted with ethyl acetate (2×50 mL)
- washThe combined organic layers was washed with HCl (0.5 N, 50 mL), sodium hydrogen carbonate (50 mL, sat), brine (50 mL)
- dry with materialdried over magnesium sulfate
- customRemoval of solvent
Sources & evidence
- ORD record
- ord-ed6c95cbcb3547ff9199afcefc4a0677
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07470723B2
Reaction notes
Loading…