Hydrochloric Acid → 2-[2-(1H-Inden-1-yl)-2-methylpropyl]pyridine
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:7].C([Li])CCC.CCCCCC.[CH3:19][C:20](=[C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23]1)[CH3:21].Cl>O1CCCC1>[CH:22]1([C:20]([CH3:21])([CH3:19])[CH2:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23]1Participants
Procedure
A solution of α-Picoline (1.97 ml, 20 mmol) in 10 ml of tetrahydrofuran was cooled to −20° C. and 15% n-butyl-lithium in hexane (13 ml, 20 mmol) was added during 10 min with stirring. The cooling bath was removed and the solution allowed to stir for 1 h while the temperature rose to room temperature. The resulting mixture was treated with a solution of 1-(1-methylethylidene)-1H-indene (3.12 g, 20 mmol) in 5 ml of tetrahydrofuran (5 ml) with vigorous stirring. The resulting solution was stirred for 14 h and hydrolyzed with 60 ml of 15-% hydrochloric acid. The organic layer was isolated and the aqueous phase washed once with ethyl acetate, then neutralized with aqueous ammonia solution and extracted three times with dichloromethane. The combined organic layers were dried over MgSO4, filtered and the solvent removed to give 4.28 g (86%) of 2-[2-(1H-inden-1-yl)-2-methylpropyl]pyridine as an oil. The product was NMR-pure, so no further distillation was necessary.
Workup
- customThe cooling bath was removed
- stirringto stir for 1 h while the temperature
- customrose to room temperature
- customThe organic layer was isolated
- washthe aqueous phase washed once with ethyl acetate
- extractionextracted three times with dichloromethane
- dry with materialThe combined organic layers were dried over MgSO4
- filtrationfiltered
- customthe solvent removed
Sources & evidence
- ORD record
- ord-79b11a98c0974124a23d44c033f6e1a5
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07541481B2
Reaction notes
Loading…