反応 #2175456

反応方程式

2,7-fluorenedicarboxylic acid dibenzyl ester

Benzyl formate

potassium tert-butoxide

→

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

溶媒

THF

反応条件

後処理

1. 1
   その他In a dry argon-purged flask
2. 2
   その他the reaction was quenched with the addition of water
3. 3
   その他The organic solvent was partially evaporated at reduced pressure
4. 4
   抽出The product was twice extracted with ethyl acetate (600 mL
5. 5
   洗浄The combined organic layers were washed three times with brine
6. 6
   乾燥dried over sodium sulfate
7. 7
   ろ過filtered
8. 8
   その他evaporated to dryness
9. 9
   洗浄The crude product was washed with hexanes and methanol (1.9 g, 60%)

実験手順

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).

出典