1-Nitrobutane → 4-Nitro-10-phenyldecan-5-one

HRID 929411

반응식

HRID 929411 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][CH3:33])([O-:29])=[O:28].C1CCN2C(=NCCC2)CC1>>[N+:27]([CH:30]([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)[CH2:31][CH2:32][CH3:33])([O-:29])=[O:28]

참가 물질

5

반응물 4

HCID 123021-NitrobutaneHCID 682631,1'-CarbonyldiimidazoleHCID 796956-Phenylhexanoic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

생성물 1

HCID 468483514-Nitro-10-phenyldecan-5-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 nitrobutane (0.080 g, 0.78 mmol) and DBU (0.198 g, 1.30 mmol) according to the general procedure. Purification by column chromatography gave 0.084 g (59%) as a yellow oil: 1H NMR (400 MHz, CDCl3) δ 7.30 (m, 2H), 7.20 (m, 3H), 5.17 (dd, J=4.4, 10.0 Hz, 1H), 2.63 (m, 4H), 1.65 (m, 6H), 1.36 (m, 4H) 1.00 (t, J=7.2 Hz, 3H) ppm; 13C NMR (100 MHz, CDCl3) δ 199.5, 142.6, 128.7, 128.6, 126.0, 94.3, 39.5, 35.9, 31.8, 31.4, 28.7, 23.3, 19.5, 13.6 ppm; IR νmax (cm−1) 3027, 2935, 2858, 1730, 1560, 1454, 1373, 1031, 749, 700; HRMS (FAB) calcd for C16H23NO3 (MNa+) 300.1570, found 300.1575.

후처리

  1. customPurification by column chromatography
  2. customgave 0.084 g (59%) as a yellow oil

출처 및 근거

ORD 기록
ord-2842739ea210470684e06fea955324e1
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09295257B2

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