1,1'-Carbonyldiimidazole → 7-Nitro-1-phenylundecan-6-one

HRID 929412노트

반응식

HRID 929412 반응식
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[N+:27]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])([O-:29])=[O:28].C1CCN2C(=NCCC2)CC1>>[N+:27]([CH:30]([CH2:31][CH2:32][CH2:33][CH3:34])[C:12](=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([O-:29])=[O:28]

참가 물질

5

반응물 4

HCID 682631,1'-CarbonyldiimidazoleHCID 796956-Phenylhexanoic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2206391-Nitropentane

생성물 1

HCID 468485147-Nitro-1-phenylundecan-6-one

실험 절차

6-Phenylhexanoic acid (0.100 g, 0.52 mmol) and CDI (0.169 g, 1.04 mmol) were added together and then reacted with nitropentane (0.091 g, 0.78 mmol) and DBU (0.198 g, 1.30 mmol) according to the general procedure. Purification by column chromatography gave 0.049 g (32%) as a yellow oil: 1H NMR (400 MHz, CDCl3) δ 7.28 (m, 2H), 7.17 (m, 3H), 5.10 (dd, J=4.4, 10.0 Hz, 1H), 2.61 (m, 4H), 1.63 (m, 6H), 1.35 (m, 6H) 0.92 (t, J=6.8 Hz, 3H) ppm; 13C NMR (100 MHz, CDCl3) δ 199.5, 142.5, 128.6, 128.5, 126.0, 94.5, 39.5, 35.9, 31.3, 29.6, 28.7, 28.1, 23.3, 22.2, 13.9 ppm; IR νmax (cm−1) 3027, 2931, 2859, 1731, 1559, 1454, 1363, 1030, 748, 700; HRMS (FAB) calcd for C17H25NO3 (MNa+) 314.1727, found 314.1722.

후처리

  1. customPurification by column chromatography
  2. customgave 0.049 g (32%) as a yellow oil

출처 및 근거

ORD 기록
ord-376bb607a3d74aca9667b45df8d90865
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09295257B2

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