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

HRID 599378

反応式

HRID 599378 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 81531Diisopropylethylamine溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-38f3654a2a024763a538dcc1083d0b8c
出典データセット
uspto-grants-2011_03
特許番号
US07897736B2

関連ノート

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