Nitromethane → 4-Chloro-2-methoxy-1-(2-nitroethenyl)benzene

反応式

[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([O:10][CH3:11])[CH:3]=1.[N+:12]([CH3:15])([O-:14])=[O:13].Cl.CN.C([O-])(=O)C.[Na+]>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[CH:15]/[N+:12]([O-:14])=[O:13])=[C:4]([O:10][CH3:11])[CH:3]=1

参加物

反応物 4

HCID 6375Nitromethane

HCID 517045Sodium Acetate

HCID 6364545Methylamine hydrochloride

HCID 138651154-Chloro-2-methoxybenzaldehyde

生成物 1

HCID 670805334-Chloro-2-methoxy-1-(2-nitroethenyl)benzene収率 78.3%

実験手順

4-Chloro-2-methoxybenzaldehyde (250 mg, 1.47 mmol) was diluted with nitromethane (556 μL, 10.3 mmol) followed by the addition of methylamine hydrochloride (59.4 mg, 0.879 mmol) and sodium acetate (72.1 mg, 0.879 mmol). After stirring for 12 hours, the reaction was loaded directly onto a biotage 25 cartridge and eluted with 5% ethyl acetate/hexanes to yield (E)-4-chloro-2-methoxy-1-(2-nitrovinyl)benzene (245 mg, 1.15 mmol, 78.3% yield).

後処理

washeluted with 5% ethyl acetate/hexanes

出典と根拠

ORDレコード: ord-1de4ca8dd7a74138848b4826cdf67e5d
出典データセット: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US09096567B2

反応ノート

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