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

HRID 1291714

반응식

HRID 1291714 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8336ad1eab3c452498747d69c5145916
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05753709

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