2-Nitrobenzaldehyde → HCID 5170752、化合物

HRID 839175ノート

反応式

HRID 839175 の反応式
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[CH:12]1([C:15]([CH3:17])=[O:16])[CH2:14][CH2:13]1>>[CH:12]1([C:15]([CH:17]=[CH:6][C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N+:1]([O-:3])=[O:2])=[O:16])[CH2:14][CH2:13]1

参加物

3

反応物 2

HCID 111012-NitrobenzaldehydeHCID 13004Cyclopropyl methyl ketone

生成物 1

HCID 5170752HCID 5170752、化合物

実験手順

2-Nitrobenzaldehyde is condensed with methyl cyclopropyl ketone to give 2-(2-nitrophenyl)vinyl cyclopropyl ketone. The latter is reduced selectively with hydroxylamine and hydroxylamine O-sulfonic acid in dilute sodium hydroxide solution to yield 2-(2-nitrophenyl)ethyl cyclopropyl ketone, which is then reduced with sodium borohydride to 2-(2-nitrophenyl)ethyl cyclopropyl carbinol. The carbinol is treated in the usual way with phosphorus tribromide and zinc bromide to afford 4-[6-(2-nitrophenyl)-3-hexenyl] bromide. The latter is reacted with potassium iodide, potassium carbonate and 3,5-heptanedione to produce 4-[6-(2-nitrophenyl)-3-hexenyl]-3,5-heptanedione which is selectively reduced with hydroxylamine and hydroxylamine O-sulfonic acid to give the title compound.

出典と根拠

ORDレコード
ord-58fde8cbf4004237bc0778553335c26c
出典データセット
uspto-grants-1978_06
特許番号
US04093736

反応ノート

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