Dimethylformamide → HCID 19934855、化合物

反応式

[CH2:1]([C:4]1[CH:9]=[C:8]([CH2:10][OH:11])[CH:7]=[C:6]([CH2:12][CH2:13][CH3:14])[C:5]=1[OH:15])[CH2:2][CH3:3].[C:16](=[O:19])([O-])[O-].[Cs+].[Cs+].CN(C)[CH:24]=[O:25]>>[CH2:1]([C:4]1[CH:9]=[C:8]([CH2:10][OH:11])[CH:7]=[C:6]([CH2:12][CH2:13][CH3:14])[C:5]=1[O:15][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:1][C:16]([O:25][CH3:24])=[O:19])[CH2:2][CH3:3]

参加物

反応物 3

HCID 6228Dimethylformamide2 回

HCID 10796Cesium carbonate

HCID 190803892,6-Di-propyl-4-hydroxymethylphenol

生成物 1

HCID 19934855HCID 19934855、化合物収率 35%

実験手順

To a solution of 1.014 g (4.87 mmol) of 2,6-di-propyl-4-hydroxymethylphenol dissolved in 10 mL of anhydrous dimethylformamide was added 2.379 g of cesium carbonate and the reaction mixture was stirred under a nitrogen atmosphere at room temperature for 1 hour. A solution of methyl cx-bromo-phenylacetate dissolved in 2 mL DMF was added and the reaction mixture was stirred at 60° C. overnight. The reaction mixture was cooled to room temperature and partitioned between water and EtOAc. The organic layer was washed with brine, separated, dried (MgSO4), filtered and evaporated. The residual oil was purified on a silica gel flash chromatography column eluted with 20% EtOAc-hexane and combination of the purified fractions afforded 0.598 g (35%) of the title compound.