반응 #2175456

반응 방정식

2,7-fluorenedicarboxylic acid dibenzyl ester

Benzyl formate

potassium tert-butoxide

→

9-formyl-2,7-fluorenedicarboxylic acid dibenzyl ester

용매

THF

반응 조건

후처리

1. 1
   기타In a dry argon-purged flask
2. 2
   기타the reaction was quenched with the addition of water
3. 3
   기타The organic solvent was partially evaporated at reduced pressure
4. 4
   추출The product was twice extracted with ethyl acetate (600 mL
5. 5
   세척The combined organic layers were washed three times with brine
6. 6
   건조dried over sodium sulfate
7. 7
   여과filtered
8. 8
   기타evaporated to dryness
9. 9
   세척The crude product was washed with hexanes and methanol (1.9 g, 60%)

실험 절차

In a dry argon-purged flask, 2,7-fluorenedicarboxylic acid dibenzyl ester (3.0 g, 0.0065 mol) was dissolved in anh. THF (60 mL) at room temperature. Benzyl formate (4.2 mL, 0.035 mol, stored over anhydrous K2CO3) was added followed by addition of potassium tert-butoxide 95% (2.7 g, 0.023 mol). The reaction was stirred for three hours then the reaction was quenched with the addition of water and acidified with HCl to pH 2. The organic solvent was partially evaporated at reduced pressure. The product was twice extracted with ethyl acetate (600 mL then 200 mL). The combined organic layers were washed three times with brine, dried over sodium sulfate, filtered and evaporated to dryness. The crude product was washed with hexanes and methanol (1.9 g, 60%). 1H-NMR (d6-DMSO): δ (ppm) 11.9 (s, ˜1H, formyl); 8.8 (s, 1H, Ar); 8.5 (s, 1H, Ar); 8.4 (s, 1H, Ar); 8.2 (m, 2H, Ar); 7.9 (m, 2H, Ar); 7.5-7.4 (m, 10H, Bz); 5.4 (s, 4H, Ar).

출처