Allyl iodide → (trans)-N-[[2-[3-(2-Propenyloxy)phenyl]cyclopropyl]methyl]butanamide

HRID 1419952Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1419952
[CH:1](/OC1C=CC=CC=1C1(CNC(=O)CCC)CC1)=[CH:2]\[CH3:3].[OH:21][C:22]1[CH:23]=[C:24]([C@@H:28]2[CH2:30][C@H:29]2[CH2:31][NH:32][C:33](=[O:37])[CH2:34][CH2:35][CH3:36])[CH:25]=[CH:26][CH:27]=1.[OH-].[K+].C(I)C=C>C(O)C.CCOCC>[CH2:3]([O:21][C:22]1[CH:23]=[C:24]([C@@H:28]2[CH2:30][C@H:29]2[CH2:31][NH:32][C:33](=[O:37])[CH2:34][CH2:35][CH3:36])[CH:25]=[CH:26][CH:27]=1)[CH:2]=[CH2:1]

Komponenten

7

Edukt 4

HCID 11166Allyl iodideHCID 14797Potassium HydroxideHCID 70274674HCID 70274674, VerbindungHCID 86754003(trans)-N-[[(2-Propen-1-yloxyphenyl)cyclopropyl]methyl]butanamide

Produkt 1

HCID 15860313(trans)-N-[[2-[3-(2-Propenyloxy)phenyl]cyclopropyl]methyl]butanamideAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

(trans)-N-[[(2-Propen-1-yloxyphenyl)cyclopropyl]methyl]butanamide: To a rapidly stirred solution of (trans)-N-[[2-(3 hydroxyphenyl)cyclopropyl]methyl]butanamide (0.8 g, 3.4 mmol) and KOH (210 mg, 3.74 mmol) in ethanol (15 mL) was added allyl iodide (622 mg, 3.7 mmol). After stirring for 18 h, the suspension was diluted with Et2O (100 mL), and washed with H2O, 2N NaOH, brine, dried (K2CO3), and concentrated to a give a crude residue. The resulting material was purified by chromatography (silica gel, 40% EtOAc/hexane) to afford 320 mg (34%) of the title compound: 1H NMR (300 MHz, CDCl3) δ 0.70-0.94 (m, 5H), 1.12-1.32 (m, 1H), 1.58-1.84 (m, 3H), 2.20 (t, J=6.0 Hz, 2H), 3.15-3.36 (m, 2H), 4.48 (d, J=5.6 Hz, 2H), 5.24 (d, J=10.0 Hz, 1H), 5.40 (d, J=17.2 Hz, 1H), 5.56 (br s, 1H), 5.96-6.07 (m, 1H), 6.57-6.70 (m, 3H), 7.13 (t, J=7.2 Hz, 1H); IR (NaCl Film) 3296, 2962, 1644, 1607, 1548, 1494 cm-1 ; MS m/e 273; Analysis calc'd for C17H23NO2 0.20(H2O): C, 73.72; H, 8.52; N, 5.06; found: C, 73.77; H, 8.63; N, 5.00.

Aufarbeitung

  1. washwashed with H2O, 2N NaOH, brine
  2. dry with materialdried (K2CO3)
  3. concentrationconcentrated to
  4. customa give a crude residue
  5. customThe resulting material was purified by chromatography (silica gel, 40% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-e594b70a9799491e805fd8fde2031cec
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05889031

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