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

HRID 1419952Notes

Reaction equation

HRID 1419952 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

(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.

Workup

  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)

Sources & evidence

ORD record
ord-e594b70a9799491e805fd8fde2031cec
Source dataset
uspto-grants-1999_03
Patent number
US05889031

Reaction notes

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