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

HRID 1475632ノート

反応式

HRID 1475632 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b4b7b6379ce24be7898de4d912699fac
出典データセット
uspto-grants-2015_04
特許番号
US09018258B2

反応ノート

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