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

HRID 632931ノート

反応式

HRID 632931 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d85bae9eaf224c7da63663a9bcb4f1f1
出典データセット
uspto-grants-2016_04
特許番号
US09321728B2

反応ノート

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