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

HRID 1291714

Reaction equation

HRID 1291714 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[CH2:10][C@H:9]2[CH2:11][NH:12][C:13](=[O:17])[CH2:14][CH2:15][CH3:16])[CH:5]=[CH:6][CH:7]=1.[OH-].[K+].[CH2:20](I)[CH:21]=[CH2:22]>C(O)C.CCOCC>[CH2:22]([O:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[CH2:10][C@H:9]2[CH2:11][NH:12][C:13](=[O:17])[CH2:14][CH2:15][CH3:16])[CH:5]=[CH:6][CH:7]=1)[CH:21]=[CH2:20]

Participants

6

Reactant 3

HCID 11166Allyl iodideHCID 14797Potassium HydroxideHCID 70274674HCID 70274674, compound

Product 1

HCID 15860313(trans)-N-[[2-[3-(2-Propenyloxy)phenyl]cyclopropyl]methyl]butanamideYield 34.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

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) δ0.70-0.94 (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-8336ad1eab3c452498747d69c5145916
Source dataset
uspto-grants-1998_05
Patent number
US05753709

Linked notes

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