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

HRID 412707노트

반응식

HRID 412707 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

HCID 196227134-(2-Ethoxycarbonylphenoxy)butyric acid수율 95.2%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-2c1b868d5b6f49fc8f57fac738fa72fa
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06562854B2

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