Triethylamine → 2,2-Dimethyl-5-oxo-2,5-dihydrofuran-3-yl trifluoromethanesulfonate

HRID 537909

반응식

HRID 537909 반응식
[OH:1][C:2]1[C:6]([CH3:8])([CH3:7])[O:5][C:4](=[O:9])[CH:3]=1.C(N(CC)CC)C.[O:17](S(C(F)(F)F)(=O)=O)[S:18]([C:21]([F:24])([F:23])[F:22])(=O)=[O:19]>C(Cl)Cl>[F:22][C:21]([F:24])([F:23])[S:18]([O:1][C:2]1[C:6]([CH3:8])([CH3:7])[O:5][C:4](=[O:9])[CH:3]=1)(=[O:19])=[O:17]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 547201394-Hydroxy-5,5-dimethyl-2(5H)-furanone

생성물 1

HCID 589263482,2-Dimethyl-5-oxo-2,5-dihydrofuran-3-yl trifluoromethanesulfonate수율 89%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-78 °C

실험 절차

To a −78° C. stirred solution of 4-hydroxy-5,5-dimethyl-5H-furan-2-one (250 mg, 1.95 mmol) in 18 mL of anhydrous CH2Cl2, was added triethylamine (0.40 mL, 2.9 mmol) and Tf2O (0.49 mL, 2.9 mmol). The reaction was stirred at −78° C. for 30 minutes, and quenched with saturated NH4Cl solution (10 mL). The mixture was warmed up to room temperature and separated. The aqueous layer was extracted with CH2Cl2 (2×20 mL). All organic layers were combined, dried over Na2SO4 and evaporated to brown oil, which was purified by plugging through a short pad of silica gel column with EtOAc/hexanes (1/3). Evaporation of solvents gave 2,2-dimethyl-5-oxo-2,5-dihydrofuran-3-yl trifluoromethanesulfonate as a light brown oil (450 mg, 89%).

후처리

  1. customquenched with saturated NH4Cl solution (10 mL)
  2. temperatureThe mixture was warmed up to room temperature
  3. customseparated
  4. extractionThe aqueous layer was extracted with CH2Cl2 (2×20 mL)
  5. dry with materialdried over Na2SO4
  6. customevaporated to brown oil, which
  7. customwas purified
  8. customEvaporation of solvents

출처 및 근거

ORD 기록
ord-dbf4dfca10f742b8b68d1a2721a6fb16
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865682B2

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