(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acid → Methyl 2-(4-(trifluoromethyl)phenyl)acetate

HRID 1475632노트

반응식

HRID 1475632 반응식
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.[CH3:15][Si](C=[N+]=[N-])(C)C>C1(C)C=CC=CC=1.CO.C(OCC)C>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([O:12][CH3:15])=[O:11])=[CH:7][CH:8]=1

참가 물질

6

반응물 2

HCID 118342(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acidHCID 167693Trimethylsilyldiazomethane

생성물 1

HCID 12717573Methyl 2-(4-(trifluoromethyl)phenyl)acetate

시약·촉매·용매 3

HCID 887Methanol용매HCID 1140Toluene용매HCID 3283Diethyl Ether용매

실험 절차

6.0 g (29.4 mmol) of [4-(trifluoromethyl)phenyl]acetic acid were dissolved in 67.1 ml of toluene and 46.2 ml of methanol, and 26.5 ml (52.9 mmol) of a 2 M solution of trimethylsilyldiazomethane in diethyl ether were added dropwise with cooling. After the addition had ended, cooling was removed and the mixture was stirred at RT for another 1 h, after which excess trimethylsilyldiazomethane was destroyed by addition of 2.0 ml of acetic acid. The reaction mixture was concentrated under reduced pressure and the crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 80:1). This gave 4.33 g of the target compound (67.6% of theory).

후처리

  1. temperaturewith cooling
  2. additionAfter the addition
  3. temperaturecooling
  4. customwas removed
  5. customafter which excess trimethylsilyldiazomethane was destroyed by addition of 2.0 ml of acetic acid
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. customthe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 80:1)

출처 및 근거

ORD 기록
ord-b4b7b6379ce24be7898de4d912699fac
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018258B2

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