Succinic anhydride → Succinic acid Fluorenylmethyl Ester

HRID 440452

반응식

HRID 440452 반응식
[C:1]1([CH2:14][OH:15])[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.CN(C1C=CC=CN=1)C.[C:25]1(=[O:31])[O:30][C:28](=[O:29])[CH2:27][CH2:26]1>N1C=CC=CC=1>[C:1]1([CH2:14][O:15][C:25](=[O:31])[CH2:26][CH2:27][C:28]([OH:30])=[O:29])[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 3

HCID 7922Succinic anhydrideHCID 218852-DimethylaminopyridineHCID 523071-Fluorenemethanol

생성물 1

HCID 69916676Succinic acid Fluorenylmethyl Ester수율 64.4%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

Fluorenylmethanol (0.90 g, 4.5 mmol) and dimethylaminopyridine (50 mg) were dissolved in 10 ml dry pyridine. Succinic anhydride (0.50 g, 5.0 mmol) was added and the solution stirred overnight. The solvent was removed under reduced pressure, sodium bicarbonate added (50 ml), the solution extracted with ethyl acetate (50 ml), and the organic layer discarded. The aqueous layer was acidified to pH 2, extracted with ethyl acetate (2×100 ml), washed with brine, and the solvent removed under reduced pressure. The residue was purified by flash chromatography (ethyl acetate/hexane 2:1 as eluant) to give 0.86 g product (2.9 mmol, 64%). 1H NMR: (CDCl3, 200 MHz) δ7.8-7.26 (8H, m, ArH), 4.43 (2H, d, J=6.5 Hz, CHCH2OCO), 4.23 (1H, t, J=6.5 Hz, CHCH2OCO), 2.70 (4H, s, OCOCH2CH2COO).

후처리

  1. customThe solvent was removed under reduced pressure, sodium bicarbonate
  2. additionadded (50 ml)
  3. extractionthe solution extracted with ethyl acetate (50 ml)
  4. extractionextracted with ethyl acetate (2×100 ml)
  5. washwashed with brine
  6. customthe solvent removed under reduced pressure
  7. customThe residue was purified by flash chromatography (ethyl acetate/hexane 2:1 as eluant)

출처 및 근거

ORD 기록
ord-99abc67d5cec4c7e907ea4893a023835
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05519134

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