Réaction #67564

Équation de réaction

glutaric anhydride

(9H-fluoren-9-yl)methanol

→

acid 151

Rendement 61.0%

4-(((9H-Fluoren-9-yl)methoxy)carbonyl)butanoic acid

Rendement 61.0%

Solvants

CH2Cl2

Conditions de réaction

Traitement

1. 1
   ConcentrationThe reaction mixture was concentrated
2. 2
   workup.ADDITIONdiluted with H2O and saturated NaHCO3 solution
3. 3
   Lavagewashed with ethyl acetate
4. 4
   ExtractionThe organic layer was extracted with saturated NaHCO3 solution (3×)
5. 5
   Extractionextracted with a 4:1 mixture of CHCl3/i-PrOH (3×′)
6. 6
   Séchagedried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated to dryness

Mode opératoire

To a solution of glutaric anhydride (1.0 g, 8.76 mmol) and (9H-fluoren-9-yl)methanol (1.56 g, 7.97 mmol) in CH2Cl2 (44 mL) was added DMAP (107 mg, 0.88 mmol) and the mixture was stirred for 20 h at room temperature. The reaction mixture was concentrated, diluted with H2O and saturated NaHCO3 solution and washed with ethyl acetate. The organic layer was extracted with saturated NaHCO3 solution (3×). The combined aqueous layers were acidified to pH=2 with conc. HCl solution, extracted with a 4:1 mixture of CHCl3/i-PrOH (3×′). The organic layers were combined, dried over MgSO4, filtered and concentrated to dryness, yielding acid 151 as a white solid (1.5 g, 61%). 1H NMR (400 MHz, CDCl3) δ 1.95 (quint, J=7.3 Hz, 2H), 2.40 (t, J=7.3 Hz, 2H), 2.47 (t, J=7.3 Hz, 2H), 4.21 (t, J=6.9 Hz, 1H), 4.43 (d, J=7.0 Hz, 2H), 7.32 (dt, J=7.4, 1.1 Hz, 2H), 7.41 (t, J=7.4 Hz, 2H), 7.59 (d, J=7.5 Hz, 2H), 7.78 (d, J=7.5 Hz, 2H).

Source