Reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=1.[C:20](OCC)(=[O:29])[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1>O1CCCC1.CCCCCC.O>[CH3:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([C:20](=[O:29])[CH2:19][C:15]2[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=2)=[CH:22][CH:23]=1Participants
Conditions
- Temperature
- -5 °C
Procedure
To a stirred solution of diisopropylamine (33.2 mL) in dry tetrahydrofuran (300 mL) cooled at −78° C., was added a solution of 1.6 M n-butyllithium in hexane (148 mL) dropwise. After addition, the resulting mixture was stirred for 10 min at the same temperature, followed by the addition of β-picoline (20 g). The resulting mixture was allowed to warm up to −10-0° C. After an additional 20 min stirring, a solution of ethyl p-anisate (19.4 g) in dry tetrahydrofuran (40 mL) was added. After addition the mixture was stirred for another 1 h at ambient temperature, and water (100 mL) was added to the mixture. The solvent was removed under reduced pressure and the oily product was extracted with ethyl acetate. The extracts were washed with water, dried, and concentrated under reduced pressure. The crystalline residue was recrystallized from ethyl acetate—isopropyl ether to afford the title compound (20.8 g, yield 85%).
Workup
- additionAfter addition
- stirringAfter an additional 20 min stirring
- additionAfter addition the mixture
- stirringwas stirred for another 1 h at ambient temperature
- customThe solvent was removed under reduced pressure
- extractionthe oily product was extracted with ethyl acetate
- washThe extracts were washed with water
- customdried
- concentrationconcentrated under reduced pressure
- customThe crystalline residue was recrystallized from ethyl acetate—isopropyl ether
Sources & evidence
- ORD record
- ord-8f42e5e64998400cb5d73dd2a29a7034
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06436966B1
Linked notes
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