Nitromethane → HCID 60166733, compound

HRID 1485826Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12]([CH:21]=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+].[N+:28]([CH3:31])([O-:30])=[O:29]>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12](/[CH:21]=[CH:31]/[N+:28]([O-:30])=[O:29])=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 6375Nitromethane

HCID 517165Ammonium Acetate

HCID 60166731HCID 60166731, compound

Product 1

HCID 60166733HCID 60166733, compoundYield 98%

Conditions

Temperature: 50 °C

Procedure

Nitromethane (1.4 mL) was added to a mixture of aldehyde 6a (0.16g, 0.56 mmol) and ammonium acetate (77 mg, 1.0 mmol) and heated to 50° C. Upon completion (˜15-30 min), the reaction mixture was cooled to RT and purified without work-up by column chromatography (SiO2, 3:1, Hex:EtOAc) to afford nitrostyrene 7a as a yellow oil (182 mg, 0.55 mmol, 98%). 1H NMR (400 MHz, CDCl3) δ 8.02 (d, J=13.6 Hz, 1H), 7.64 (d, J=9.5 Hz, 1H), 7.50-7.35 (m, 10H), 7.31 (d, J=2.1 Hz, 2H), 7.04 (d, J=2.5 Hz, 1H), 5.15 (s, 2H); 13C NMR (100 MHz, CDCl3) δ 161.8, 146.1, 138.1, 136.4, 136.3, 135.5, 131.8 131.7, 129.9, 129.2, 128.8, 128.0, 121.3, 117.3, 116.3, 116.0, 115.6, 70.7; HRMS (FAB) m/z: [M+Na+] for C21H18NO3, calcd, 332.1281. found, 332.1290.

Workup

temperatureUpon completion (˜15-30 min), the reaction mixture was cooled to RT
custompurified without work-up by column chromatography (SiO2, 3:1, Hex:EtOAc)

Sources & evidence

ORD record: ord-a3d3b293d3e3424e8e0e477a19130a68
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422320B2

Reaction notes

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