Water → trans-Methyl 2-[4-[4-[(trifluoromethylsulfonyl)oxy]phenyl]cyclohexyl]acetate

HRID 632931노트

반응식

HRID 632931 반응식
C(N(CC)CC)C.[CH3:8][O:9][C:10](=[O:25])[CH2:11][CH:12]1[CH2:17][CH2:16][CH:15]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)[CH2:14][CH2:13]1.[F:26][C:27]([F:33])([F:32])[S:28](O)(=[O:30])=[O:29].O>C(Cl)Cl>[CH3:8][O:9][C:10](=[O:25])[CH2:11][CH:12]1[CH2:13][CH2:14][CH:15]([C:18]2[CH:19]=[CH:20][C:21]([O:24][S:28]([C:27]([F:33])([F:32])[F:26])(=[O:30])=[O:29])=[CH:22][CH:23]=2)[CH2:16][CH2:17]1

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 62406Trifluoromethanesulfonic acidHCID 56971748Methyl 2-((1s,4s)-4-(4-hydroxyphenyl)cyclohexyl)acetate

생성물 1

HCID 58909683trans-Methyl 2-[4-[4-[(trifluoromethylsulfonyl)oxy]phenyl]cyclohexyl]acetate수율 91.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Triethyl amine (8.1 mL, 57.99 mmol) was added dropwise to [4-(4-hydroxyphenyl)cyclohexyl]acetic acid methyl ester (9.6 g, 38.66 mmol) dissolved in CH2Cl2 and trifluoromethane sulphonic acid (8.1 mL, 48.32 mmol) solution at 0° C. The reaction mixture was warmed up to reach ambient temperature and stirred for 5 hours. The reaction mixture was poured into 200 mL water and extracted with CH2Cl2. The organic phase was washed with saturated sodium bicarbonate solution, brine and anhydrous Na2SO4. The solvent was reduced under reduced pressure, the residue was purified in silica gel using CH2Cl2 as an eluent to obtain [4-(4-trifluoromethanesulfonyloxyphenyl)cyclohexyl]acetic acid methyl ester (13.4 g, 91%) as a white solid.

후처리

  1. customat 0° C
  2. temperatureThe reaction mixture was warmed up
  3. customto reach ambient temperature
  4. extractionextracted with CH2Cl2
  5. washThe organic phase was washed with saturated sodium bicarbonate solution, brine and anhydrous Na2SO4
  6. customthe residue was purified in silica gel

출처 및 근거

ORD 기록
ord-d85bae9eaf224c7da63663a9bcb4f1f1
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321728B2

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