Trifluoroacetic acid → 4-(2-Ethoxycarbonylphenoxy)butyric acid

HRID 412707ノート

反応式

HRID 412707 の反応式
C([O:5][C:6]([CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:7])(C)(C)C.FC(F)(F)C(O)=O.C(OCC)(=O)C>C(OCC)C>[CH2:17]([O:16][C:14]([C:13]1[CH:19]=[CH:20][CH:21]=[CH:22][C:12]=1[O:11][CH2:10][CH2:9][CH2:8][C:6]([OH:7])=[O:5])=[O:15])[CH3:18]

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 18537757Ethyl 2-(3-tert-butoxycarbonylpropoxy)benzoate

生成物 1

HCID 196227134-(2-Ethoxycarbonylphenoxy)butyric acid収率 95.2%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

Ethyl 2-(3-tert-butoxycarbonylpropoxy)benzoate (3.60 g, 11.7 mmol) was treated with an excess of trifluoroacetic acid at room temperature over one hour. The solution was concentrated in vacuo and the oily residue purified by silica gel flash chromatography using (10:1) hexane:ethyl acetate to pure ethyl ether to provide 4-(2-ethoxycarbonylphenoxy)butyric acid as a colorless crystalline solid (2.81 g, 95% yield); 1H NMR (300 MHz, CDCl3): 7.80 (d, 1H), 7.50 (tr, 1H), 7.00 (m, 2H), 4.40 (q, 2H), 4.15 (tr, 2H), 2.65 (tr, 2H), 2.20 (m, 2H), 1.40 (tr, 3H).

後処理

  1. concentrationThe solution was concentrated in vacuo
  2. customthe oily residue purified by silica gel flash chromatography

出典と根拠

ORDレコード
ord-2c1b868d5b6f49fc8f57fac738fa72fa
出典データセット
uspto-grants-2003_05
特許番号
US06562854B2

反応ノート

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