Tetrahydro-4H-pyran-4-one → 4-(3,5-Difluorophenyl)oxan-4-ol

HRID 879108노트

반응식

HRID 879108 반응식
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[CH:3]=1.[O:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]1>C1COCC1>[F:9][C:4]1[CH:3]=[C:2]([C:13]2([OH:16])[CH2:14][CH2:15][O:10][CH2:11][CH2:12]2)[CH:7]=[C:6]([F:8])[CH:5]=1

참가 물질

4

반응물 2

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 1363131-Bromo-3,5-difluorobenzene

생성물 1

HCID 193886354-(3,5-Difluorophenyl)oxan-4-ol수율 71%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 1-bromo-3,5-difluorobenzene (1.6 equiv.) in THF (0.26 M) under Ar was added Mg turnings (1.6 equiv.). A reflux condenser was attached and the solution was submerged in a 90° C. oil bath and refluxed for two hours. The dihydro-2H-pyran-4(3H)-one (1.0 equiv.) was added in THF via syringe. The solution was left stirring at rt under Ar for 5 hrs. The reaction solution was quenched by addition of NH4Cl(sat) and the solution was extracted with EtOAc, washed with NaCl(sat.), dried over MgSO4, filtered, concentrated and purified by ISCO SiO2 chromatography (0-100% EtOAc/n-heptanes gradient) to yield 4-(3,5-difluorophenyl)tetrahydro-2H-pyran-4-ol in 71% yield. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.59-1.68 (m, 3H), 2.07-2.19 (m, 2H), 3.87-3.93 (m, 4H), 6.72 (tt, J=8.75, 2.20 Hz, 1H), 6.97-7.06 (m, 2H).

후처리

  1. customA reflux condenser was attached
  2. customwas submerged in a 90° C.
  3. temperaturerefluxed for two hours
  4. waitThe solution was left
  5. customThe reaction solution was quenched by addition of NH4Cl(sat)
  6. extractionthe solution was extracted with EtOAc
  7. washwashed with NaCl(sat.)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. custompurified by ISCO SiO2 chromatography (0-100% EtOAc/n-heptanes gradient)

출처 및 근거

ORD 기록
ord-c3b75c7099924bcf84a0434496c1d7f6
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987457B2

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