Ethyl 4-bromobutyrate → Ethyl 4-[(3-hydroxypropyl)phenylamino]butanoate

HRID 1006736

반응식

HRID 1006736 반응식
[C:1]1([NH:7][CH2:8][CH2:9][CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(N(C(C)C)C(C)C)C>[OH:11][CH2:10][CH2:9][CH2:8][N:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]

참가 물질

4

반응물 2

HCID 76300Ethyl 4-bromobutyrateHCID 4104673-(Phenylamino)propan-1-ol

생성물 1

HCID 66716979Ethyl 4-[(3-hydroxypropyl)phenylamino]butanoate수율 100.8%

시약·촉매·용매 1

HCID 81531Diisopropylethylamine용매

반응 조건

온도
100 °C

실험 절차

A mixture of 3-(phenylamino)propan-1-ol (Huang, et al., J.Org.Chem.; 58(23):6235-6246(1993)) (65.6 g, 0.43 mol), ethyl 4-bromobutyrate (104.5 g, 0.54 mol) and 100 mL of ethyldiisopropylamine is stirred at 100° C. for 1 h. The reaction is cooled to room temperature and partitioned between water 400 mL and ethyl acetate (500 mL). The organic layer is washed with saturated NaHCO3, brine and dried over Na2SO4. The oil obtained after concentration is chromatographed on silica eluting with 10% EtOH/CHCl3. Concentration of the appropriate fractions affords 115 g (100%) of the desired product as a colorless, viscous oil. 1H NMR (CDCl3) δ 7.23 (m, 2H), 6.72 (m, 3H), 4.14 (q, J=7 Hz, 2H), 3.72 (t, J=6 Hz, 2H), 3.43 (t, 7 Hz, 2H), 3.34 (t, 7 Hz, 2H), 2.35 (t, 7 Hz), 1.88 (m, 4H), 1.26 (t, 7 Hz, 3H).

후처리

  1. temperatureThe reaction is cooled to room temperature
  2. custompartitioned between water 400 mL and ethyl acetate (500 mL)
  3. washThe organic layer is washed with saturated NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. customThe oil obtained
  6. concentrationafter concentration
  7. customis chromatographed on silica eluting with 10% EtOH/CHCl3

출처 및 근거

ORD 기록
ord-95c11b2babd749d6a794139d62d564b1
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06790945B2

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