tert-Butoxy bis(dimethylamino)methane → alpha-[3-(Dimethylamino)-2-propenylidene]-3-pyridineacetonitrile
Reaction equation
[CH:1](=[C:3]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[C:4]#[N:5])[CH3:2].C(O[CH:17](N(C)C)[N:18]([CH3:20])[CH3:19])(C)(C)C>O1CCCC1>[CH3:17][N:18]([CH3:20])[CH:19]=[CH:2][CH:1]=[C:3]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[C:4]#[N:5]Participants
4
Conditions
- Temperature
- 20 °C
Procedure
A 0.2 g portion of α-ethylidene 3-pyridine acetonitrile and 0.315 ml of t-butoxy-bis-dimethylaminomethane were dissolved in tetrahydrofuran and stirred at 20° C. for 20 hours. The solvent was removed at reduced pressure and the orange oil was purified by chromatography, eluting with ethyl acetate:hexane (10:3). The eluate was concentrated to a solid which was recrystallized from methylene chloride-hexane, giving α-[3-(dimethylamino)-2-propenylidene]-3-pyridineacetonitrile as yellow crystals, mp 117°-120° C.
Workup
- customThe solvent was removed at reduced pressure
- customthe orange oil was purified by chromatography
- washeluting with ethyl acetate:hexane (10:3)
- concentrationThe eluate was concentrated to a solid which
- customwas recrystallized from methylene chloride-hexane
Sources & evidence
- ORD record
- ord-1009b698b2d64f739b8835ceaa50763f
- Source dataset
- uspto-grants-1985_10
- Patent number
- US04550166
Reaction notes
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