반응 #217530

반응 방정식

3-(trifluoromethyl)-benzaldehyde

2-(3-bromophenyl)-1,3-dioxolane

2-(3-bromophenyl)-1,3-dioxolane

magnesium

NH4Cl

→

(3-(1,3-dioxolan-2-yl)phenyl)[3-(trifluoromethyl)phenyl]-methan-1-ol

용매

THF

THF

THF

반응 조건

후처리

1. 1
   workup.WAITat 50-60° C. for 20 hours
2. 2
   온도After the mixture is cooled
3. 3
   workup.STIRRINGthe reaction is stirred at room temp for 24 hours
4. 4
   workup.STIRRINGstirred for 30 minutes
5. 5
   기타The organic layer is separated
6. 6
   추출the aqueous layer is extracted with ethyl acetate (2×100 mL)
7. 7
   건조dried over anhydrous Na2SO4
8. 8
   기타The solvent is removed
9. 9
   기타the residue is purified by column chromatography on silica gel
10. 10
    세척Eluting with ethyl acetate/hexanes (20:80)

실험 절차

A 1.0 mL aliquot of 2-(3-bromophenyl)-1,3-dioxolane is added into magnesium (610 mg; 25 mmol) and THF (5 mL) under Argon. After the reaction is started, the residue of 2-(3-bromophenyl)-1,3-dioxolane (total: 5.73 g; 25 mmol) in THF (20 mL) is added dropwise into the reaction mixture. The resulting solution is stirred at room temp for six hours, and then at 50-60° C. for 20 hours. After the mixture is cooled, a solution of 3-(trifluoromethyl)-benzaldehyde (4.35 g; 25 mmol) in THF (20 mL) is added dropwise and the reaction is stirred at room temp for 24 hours. A saturated solution of NH4Cl (50 mL) is added and stirred for 30 minutes. The organic layer is separated and the aqueous layer is extracted with ethyl acetate (2×100 mL). The organic layers are combined and dried over anhydrous Na2SO4. The solvent is removed and the residue is purified by column chromatography on silica gel. Eluting with ethyl acetate/hexanes (20:80) provide a colorless oil (3.23 g; 40%) as (3-(1,3-dioxolan-2-yl)phenyl)[3-(trifluoromethyl)phenyl]-methan-1-ol: MS 307.0 (M−17).

출처