Calcium Carbonate → 1,4-Dimethoxy-3-bromo-2-hydroxymethylnaphthalene

反応式

[Br:1][C:2]1[C:11]([CH2:12]Br)=[C:10]([O:14][CH3:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[O:16][CH3:17].C([O-])([O-])=[O:19].[Ca+2]>COCCOC.O>[Br:1][C:2]1[C:11]([CH2:12][OH:19])=[C:10]([O:14][CH3:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[O:16][CH3:17]

参加物

実験手順

Following a modified procedure of Smith et al.,25 dibromide 36 (1.73 g, 4.80 mmol) was dissolved in 1,2-dimethoxyethane (50.0 mL), and then added to CaCO3 (2.50 g, 25.0 mmol) in H2O (50.0 mL) at room temperature. The reaction was heated under reflux for TIME and then cooled to room temperature. The reaction was extracted with EtOAc (75.0 mL), and the organic layers are washed with brine. The organic layer was dried over MgSO4 and filtered. The resulting pink solid was then purified by flash column chromatography (1:3 EtOAc:hexanes) to provide 37 (1.49 g, 5.01 mmol, 105%) as a pink solid.