Propynal → (E)-3-[4,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazol-1-yl]-2-propenal

HRID 2050579

反応式

HRID 2050579 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:20]([CH3:22])[CH3:21])[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[CH:23](=[O:26])[C:24]#[CH:25]>C1COCC1.CC(C)=O>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]2[N:11]=[C:10]([CH:20]([CH3:22])[CH3:21])[N:9](/[CH:25]=[CH:24]/[CH:23]=[O:26])[C:8]=2[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:14][CH:15]=1

参加物

5

反応物 2

HCID 12222PropynalHCID 148497764,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazole

生成物 1

HCID 14849786(E)-3-[4,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazol-1-yl]-2-propenal

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 4,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazole (200 mg) and propiolaldehyde (75% solution in toluene, 0.15 ml) in dry THF (15 ml) were heated under reflux, under nitrogen for 24 h. The residue was dissolved in acetone and absorbed onto silica gel before purifying by CC eluting with petroleum ether (b.p. 40°-60°)/ethyl acetate (2:1) to give the title compound (84 mg) as a pale yellow solid, δ(CDCl3), 1.49 (d, J=7 Hz, Me2CH), 3.25 (septet, J=7 Hz, Me2CH), 5.67 (dd, J=15 Hz, 7 Hz, CH=CH.CHO), 6.95 and 7.10-7.60 (t, J=9 Hz and m, CH=CH.CHO and aromatic protons), 9.40 (d, J=7 Hz, CH=CH.CHO).

後処理

  1. temperatureunder reflux, under nitrogen for 24 h
  2. customabsorbed onto silica gel
  3. custombefore purifying by CC
  4. washeluting with petroleum ether (b.p. 40°-60°)/ethyl acetate (2:1)

出典と根拠

ORDレコード
ord-5322d1d63ca74e688924c062f834ef93
出典データセット
uspto-grants-1991_05
特許番号
US05013749

関連ノート

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