반응 #829486

반응 방정식

hydrogen peroxide

NaOH

9-borabicyclo[3.3.1]nonane

t-butyl 4-vinylbenzoate

→

t-butyl 4-(2-hydroxyethyl)benzoate

용매

tetrahydrofuran

water

water

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGThe obtained mixture was stirred as such for one hour
2. 2
   기타The mixture thus obtained
3. 3
   추출was extracted with ethyl acetate
4. 4
   세척The organic phase was washed with an aqueous solution of common salt
5. 5
   workup.DISTILLATIONdistilled
6. 6
   기타to remove the solvent
7. 7
   기타The obtained residue was purified by silica gel column chromatography (developer: n-hexane/ethyl acetate=1:1)
8. 8
   기타to give the objective compound

실험 절차

A solution of 9-borabicyclo[3.3.1]nonane (9-BBN, 5.65 g, 46.3 mmol) in anhydrous tetrahydrofuran was added to a solution of t-butyl 4-vinylbenzoate (8.47 g, 42.1 mmol) prepared in the Preparative Example 102 in anhydrous tetrahydrofuran in a nitrogen stream. The obtained mixture was stirred at room temperature for 3 hours. 15 ml of water and 17 ml of 3N NaOH were added to the reaction mixture successively, followed by the dropwise addition of 30% aqueous hydrogen peroxide at 50° C. or below. The obtained mixture was stirred as such for one hour and poured into water. The mixture thus obtained was extracted with ethyl acetate. The organic phase was washed with an aqueous solution of common salt, dehydrated and distilled to remove the solvent. The obtained residue was purified by silica gel column chromatography (developer: n-hexane/ethyl acetate=1:1) to give the objective compound. yield: 8.71 g

출처