Water → Ethyl 3-methyl-3-pyridin-4-ylprop-2-enoate

反応式

[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]

参加物

反応物 4

HCID 962Water

HCID 8028Tetrahydrofuran

HCID 142824-Acetylpyridine

HCID 2733832Lithium hexamethyldisilazane

生成物 1

HCID 69315756Ethyl 3-methyl-3-pyridin-4-ylprop-2-enoate

実験手順

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.