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

HRID 39286

반응식

HRID 39286 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0287c114f0094080b7f5d9645e2e173e
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524691B2

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