Benzyl formate → 9-Formyl-2,7-fluorenedicarboxylic acid dibenzyl ester

HRID 2367874Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2367874
[CH2:1]([O:8][C:9]([C:11]1[CH:23]=[CH:22][C:21]2[C:20]3[C:15](=[CH:16][C:17]([C:24]([O:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[O:25])=[CH:18][CH:19]=3)[CH2:14][C:13]=2[CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:34](OCC1C=CC=CC=1)=[O:35].CC(C)([O-])C.[K+]>C1COCC1>[CH2:27]([O:26][C:24]([C:17]1[CH:18]=[CH:19][C:20]2[C:21]3[C:13](=[CH:12][C:11]([C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:10])=[CH:23][CH:22]=3)[CH:14]([CH:34]=[O:35])[C:15]=2[CH:16]=1)=[O:25])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Komponenten

5

Edukt 3

HCID 7708Benzyl formateHCID 23665647Potassium tert-butoxideHCID 66910038Dibenzyl 9H-fluorene-2,7-dicarboxylate

Produkt 1

HCID 866097799-Formyl-2,7-fluorenedicarboxylic acid dibenzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. customIn a dry argon-purged flask
  2. customthe reaction was quenched with the addition of water
  3. customThe organic solvent was partially evaporated at reduced pressure
  4. extractionThe product was twice extracted with ethyl acetate (600 mL
  5. washThe combined organic layers were washed three times with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. washThe crude product was washed with hexanes and methanol (1.9 g, 60%)

Quellen und Nachweise

ORD-Eintrag
ord-64993386b02c4e208ce7ebf6b32877c1
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703115B2

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