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

HRID 929411

Reaction equation

[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]

Participants

Reactant 4

HCID 123021-Nitrobutane

HCID 682631,1'-Carbonyldiimidazole

HCID 796956-Phenylhexanoic Acid

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 468483514-Nitro-10-phenyldecan-5-one

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-2842739ea210470684e06fea955324e1
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09295257B2

Linked notes

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