Trifluoromethanesulfonic acid → HCID 13611241, 화합물

HRID 1093097

반응식

HRID 1093097 반응식
[OH:1][CH:2]1[CH2:6][O:5][C:4](=[O:7])[CH2:3]1.ClC(Cl)(Cl)C(=N)O[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.FC(F)(F)S(O)(=O)=O>C(Cl)Cl.C1CCCCC1>[CH2:12]([O:1][CH:2]1[CH2:6][O:5][C:4](=[O:7])[CH2:3]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

6

반응물 3

HCID 62406Trifluoromethanesulfonic acidHCID 956523,4-Dihydroxybutanoic acid gamma-lactoneHCID 144968Benzyl 2,2,2-trichloroacetimidate

생성물 1

HCID 13611241HCID 13611241, 화합물수율 75.5%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8078Cyclohexane용매

반응 조건

온도
0 °C

실험 절차

To a stirred solution of 4-hydroxydihydrofuran-2(3H)-one (25 g, 245 mmol) and benzyl 2,2,2-trichloroacetimidate (68.6 mL, 367 mmol) in CH2Cl2 (500 mL) and cyclohexane (500 mL) at 0° C. was added, dropwise, trifluoromethanesulfonic acid (2.175 mL, 24.49 mmol) over 10 min. The reaction mixture was stirred for 2 h at 0° C. and 48 h at room temperature. After this, it was diluted with hexanes (0.75 L), filtered and the filtrate washed with sat. aq. NaHCO3 (150 mL), dried (Na2SO4), filtered and concentrated. The resulting yellow oil was purified by flash column chromatography on silica gel column using 5-40% ethyl acetate/hexane (5% increment for every liter) to afford 4-(benzyloxy)dihydrofuran-2(3H)-one (35.52 g, 185 mmol, 75% yield) as a clear yellow oil. 1H NMR (500 MHz, CDCl3) δ: 7.34-7.39 (2 H, m), 7.29-7.34 (3 H, m), 4.53 (1 H, d, JAB=11.9 Hz), 4.52 (1 H, d, JAB=11.90 Hz), 4.34-4.41 (3 H, m), 2.64-2.68 (2 H, m).

후처리

  1. filtrationfiltered
  2. washthe filtrate washed with sat. aq. NaHCO3 (150 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting yellow oil was purified by flash column chromatography on silica gel column

출처 및 근거

ORD 기록
ord-961835292e8c4ed197f7721997674b0e
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129398B2

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