반응 #1009458

반응 방정식

5-(4-hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

cyclopropylmagnesium bromide

→

5-[Cyclopropyl(4-hydroxyphenyl)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione

수율 42.8%

용매

THF

반응 조건

후처리

1. 1
   기타To a 250 mL RB flask fitted with magnetic stirrer
2. 2
   기타Then, the reaction mass was quenched with 20 mL of 1N HCl
3. 3
   workup.ADDITIONethyl acetate (50 mL) was added
4. 4
   workup.STIRRINGstirred well
5. 5
   기타the layers were separated
6. 6
   세척The organic layer was washed with water (100 mL×3), brine solution
7. 7
   건조Then the organic layer was dried over anhydrous Na2SO4
8. 8
   기타The solvent was removed under reduced pressure
9. 9
   기타the resulting crude compound is purified by column chromatography on silica gel (60-120 meshes)
10. 10
    기타The product was obtained as yellow solid

실험 절차

To a 250 mL RB flask fitted with magnetic stirrer was charged 6 mL of dry THF under argon atmosphere. To the stirred solvent was added 5-(4-hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (0.6 g, 2.41 mmol). The resulting mixture was cooled to 0° C. and was added cyclopropylmagnesium bromide (25 mL, 0.5 M in THF, 7.25 mmol). The resulting mixture was stirred at ambient temperatures for 2 h. Then, the reaction mass was quenched with 20 mL of 1N HCl then, ethyl acetate (50 mL) was added, stirred well and the layers were separated. The organic layer was washed with water (100 mL×3), brine solution. Then the organic layer was dried over anhydrous Na2SO4. The solvent was removed under reduced pressure, and the resulting crude compound is purified by column chromatography on silica gel (60-120 meshes) using petroleum ether (60-80) and ethyl acetate as eluent. The product was obtained as yellow solid. Yield: 42.76% (0.3 g) MS (ESI, 120 ev): m/z=291.1 (M+1). (300 MHz, DMSO-d6): δ 9.16 (s, 1H), 6.95-6.98 (d, 2H), 6.53-6.56 (d, 2H), 4.42-4.43 (d, 1H), 2.54-2.59 (m, 1H), 1.61 (s, 4H), 1.29 (s, 3H), 0.40-0.49 (m, 2H), 0.23-0.28 (m, 1H), 0.03-0.01 (m, 1H).

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