Trifluoroacetic acid → [4-(Acetoxymethyl)phenyl](cyclopentyl)acetic acid

HRID 877188ノート

反応式

HRID 877188 の反応式
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[C:13]([O:15]C(C)(C)C)=[O:14])=[CH:8][CH:7]=1)(=[O:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[C:13]([OH:15])=[O:14])=[CH:8][CH:7]=1)(=[O:3])[CH3:2]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 58136319Tert-butyl [4-(acetoxymethyl)phenyl](cyclopentyl)acetate

生成物 1

HCID 58136423[4-(Acetoxymethyl)phenyl](cyclopentyl)acetic acid収率 111%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

13.27 g (37.2 mmol, 95% pure) of tert-butyl(+/−)-{4-[(acetyloxy)methyl]phenyl}(cyclopentyl)acetate were dissolved in 117 ml of dichloromethane, the mixture was cooled to 0° C. and 58.4 ml of trifluoroacetic acid were added. The reaction mixture was initially stirred at 0° C. for 1.5 h and then at RT for a further 1.5 h. The mixture was then concentrated under reduced pressure and the residue was dried under high vacuum. The residue was taken up in 50 ml of dichloromethane, and the solution was washed four times with water. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure. Drying under high vacuum gave 11.41 g of the title compound which were used without further purification for the next reaction.

後処理

  1. waitat RT for a further 1.5 h
  2. concentrationThe mixture was then concentrated under reduced pressure
  3. customthe residue was dried under high vacuum
  4. washthe solution was washed four times with water
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customDrying under high vacuum

出典と根拠

ORDレコード
ord-85362638eb3d43feafcd2d3360908f10
出典データセット
uspto-grants-2015_03
特許番号
US08987256B2

反応ノート

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