Water → Ethyl 3-methyl-3-pyridin-4-ylprop-2-enoate
Reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)(=O)[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[OH2:20].[CH2:21]1[CH2:25][O:24][CH2:23][CH2:22]1>>[CH3:2][C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)=[CH:22][C:23]([O:24][CH2:25][CH3:21])=[O:20]Participants
5
Procedure
4-Acetyl pyridine (9 ml, 83 mmol) was added to a cooled solution of triethylphosphonoacetate (16.5 ml, 83 mmol) and lithium bis(trimethylsilyl)amide (1 M in THF, 90 ml, 90 mmol) in THF (100 ml) at 0° C. The mixture was allowed to warm to room temperature and poured into water. The mixture was extracted with EtOAc. The organic layers were dried and evaporated in vacuo. The crude product was purified by chromatography eluting with 30-50% EtOAc in hexane to give the product as a yellow oil. M/z 192.
Workup
- extractionThe mixture was extracted with EtOAc
- customThe organic layers were dried
- customevaporated in vacuo
- customThe crude product was purified by chromatography
- washeluting with 30-50% EtOAc in hexane
Sources & evidence
- ORD record
- ord-2455604e2947412a8975b3735a66fd50
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07332492B2
Reaction notes
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