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

HRID 2087111

Reaktionsgleichung

[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]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A mixture of 3-(phenylamino)propan-1-ol (Huang, Yande; Arif, Atta M.; Bentrude, Weseley G.; J.Org.Chem.; 58; 23; 1993; 6235-6246) (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=6Hz, 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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-9a280b849c7a4928a6fc5d61f23f20ae
Quelldatensatz: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06727356B1

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