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

HRID 39286

Reaction equation

HRID 39286 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-0287c114f0094080b7f5d9645e2e173e
Source dataset
uspto-grants-2013_09
Patent number
US08524691B2

Linked notes

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