반응 #42193

반응 방정식

(±)-tert-butyl(dimethyl)(3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-ylmethoxy)silane

tetrabutylammonium fluoride

→

(±)-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-ylmethanol

수율 91.3%

용매

water

tetrahydrofuran

반응 조건

후처리

1. 1
   추출extracted with ethyl acetate (2×150 mL)
2. 2
   세척The combined organic extracts were washed with saturated aqueous sodium chloride (400 mL)
3. 3
   건조dried (magnesium sulfate)
4. 4
   기타the solvent was removed in vacuo
5. 5
   기타to give a crude oil
6. 6
   기타Purification by flash column chromatography (silica, ethyl acetate:hexanes 1:3)

실험 절차

To a solution of (±)-tert-butyl(dimethyl)(3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-ylmethoxy)silane (2.93 g; 9.62 mmol) in tetrahydrofuran (100 mL) cooled to 0° C. was added tetrabutylammonium fluoride (10.6 mL, 1.0 M solution in tetrahydrofuran) and the reaction mixture was allowed to stir at room temperature for 8 h. The reaction mixture was diluted with water (200 mL) and extracted with ethyl acetate (2×150 mL). The combined organic extracts were washed with saturated aqueous sodium chloride (400 mL), dried (magnesium sulfate) and the solvent was removed in vacuo to give a crude oil. Purification by flash column chromatography (silica, ethyl acetate:hexanes 1:3) afforded 1.67 g (91%) of (±)-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-ylmethanol as a colorless oil. Rf=0.63 (silica, ethyl acetate:hexanes 1:2); Anal. calcd. for C12H14O2: C, 75.76; H, 7.42. Found: C, 74.46; H, 7.44.

출처