Water → 1H-Inden-1-one, 2,3-dihydro-2-(hydroxymethylene)-

반응식

[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[H-].[Na+].[CH:13](OCC)=[O:14].O>C1(C)C=CC=CC=1>[OH:14][CH:13]=[C:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:1]1=[O:10]

참가 물질

실험 절차

1-Indanone (Aldrich) (5.0 g, 37.8 mmol) in toluene (25 cm3) was added dropwise, to a stirring solution of sodium hydride (Aldrich) (1.8 g, 45.4 mmol 60% w/w dispersion in oil), ethyl formate (Aldrich) (5.6 g, 75.6 mmol) and toluene (50 cm3), under nitrogen, at 0° C. The reaction was stirred for 17 hours before adding water (50 cm3). The organic layer was washed with water and 2M NaOH. The combined aqueous extracts were acidified with 10 M HCl and the precipitate extracted with dichloromethane. The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to afford a yellow-orange solid. An analytically pure sample was obtained by Kugelrohr distillation (0.01 mmHg/100° C.) to give a yellow solid m.p. 110-112° C.