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

반응식

[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]

참가 물질

반응물 4

HCID 962Water

HCID 8028Tetrahydrofuran

HCID 142824-Acetylpyridine

HCID 2733832Lithium hexamethyldisilazane

생성물 1

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

실험 절차

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.