Реакция #2175456

Уравнение реакции

2,7-fluorenedicarboxylic acid dibenzyl ester

Benzyl formate

potassium tert-butoxide

→

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

Растворители

THF

Условия реакции

Обработка

1. 1
   ДругоеIn a dry argon-purged flask
2. 2
   Другоеthe reaction was quenched with the addition of water
3. 3
   ДругоеThe organic solvent was partially evaporated at reduced pressure
4. 4
   ЭкстракцияThe product was twice extracted with ethyl acetate (600 mL
5. 5
   ПромывкаThe combined organic layers were washed three times with brine
6. 6
   Сушкаdried over sodium sulfate
7. 7
   Фильтрацияfiltered
8. 8
   Другоеevaporated to dryness
9. 9
   ПромывкаThe crude product was washed with hexanes and methanol (1.9 g, 60%)

Методика

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).

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