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

HRID 39286

Reaktionsgleichung

Reaktionsgleichung von HRID 39286
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][CH2:3][CH2:2]1.[CH:9]1[C:21]2[CH:20]([CH2:22][OH:23])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]=2[CH:12]=[CH:11][CH:10]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH:9]1[C:21]2[CH:20]([CH2:22][O:23][C:5]([CH2:4][CH2:3][CH2:2][C:1]([OH:7])=[O:8])=[O:6])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]=2[CH:12]=[CH:11][CH:10]=1

Komponenten

5

Edukt 2

HCID 7940Glutaric anhydrideHCID 904669H-Fluorene-9-methanol

Produkt 1

HCID 221376034-(((9H-Fluoren-9-yl)methoxy)carbonyl)butanoic acidAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with H2O and saturated NaHCO3 solution
  3. washwashed with ethyl acetate
  4. extractionThe organic layer was extracted with saturated NaHCO3 solution (3×)
  5. extractionextracted with a 4:1 mixture of CHCl3/i-PrOH (3×′)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-0287c114f0094080b7f5d9645e2e173e
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524691B2

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