3-Phenylprop-2-Enal → HCID 86761424、化合物

HRID 1661520ノート

反応式

HRID 1661520 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:12](=[O:13])[C:11]3[C:14]([O:21][CH2:22][CH3:23])=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[CH:17][C:10]=3[O:9]2)=[CH:4][CH:3]=1.C[O-].[Na+].[CH:27](=[O:36])[CH:28]=[CH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[Cl-].[NH4+]>CO.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([C@H:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:28][CH:27]=[O:36])[C:12](=[O:13])[C:11]3[C:14]([O:21][CH2:22][CH3:23])=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[CH:17][C:10]=3[O:9]2)=[CH:4][CH:3]=1.[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([C@@H:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:28][CH:27]=[O:36])[C:12](=[O:13])[C:11]3[C:14]([O:21][CH2:22][CH3:23])=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[CH:17][C:10]=3[O:9]2)=[CH:4][CH:3]=1

参加物

8

反応物 4

HCID 3073-Phenylprop-2-EnalHCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 57545162HCID 57545162、化合物

生成物 2

HCID 57545213HCID 57545213、化合物HCID 86761424HCID 86761424、化合物収率 42.5%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 1140Toluene溶媒2 回

実験手順

Under argon, 20.9 g (55.4 mmol) of 2-(4-bromophenyl)-4,6-diethoxybenzofuran-3-one are dissolved in 422 ml of degassed methanol and 100 ml of degassed toluene. At RT, 2.00 g (11.1 mmol) of a 30% strength methanolic sodium methoxide solution are added. One minute later, cinnamaldehyde (9.52 g, 72.0 mmol) dissolved in 111 ml of degassed toluene is added. The mixture is stirred at RT overnight and then left to stand for 48 h. Subsequently saturated ammonium chloride solution is added and the mixture is extracted three times with dichloromethane. The combined organic phases are dried over sodium sulfate, filtered and concentrated. Column chromatography on silica gel 60 (mobile phase: toluene/ethyl acetate 95:5) results in 10.7 g (38% of theory) of the title compound as racemic mixture and 6.00 g (21% of theory) of the diastereomer (R*,R*)-3-[2-(4-bromophenyl)-4,6-diethoxy-3-oxo-2,3-dihydrobenzofuran-2-yl]-3-phenylpropanal as racemic mixture.

後処理

  1. additionis added
  2. waitleft
  3. waitto stand for 48 h
  4. extractionthe mixture is extracted three times with dichloromethane
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-1511beca22ad45e9accab8365b937496
出典データセット
uspto-grants-2011_10
特許番号
US08030347B2

反応ノート

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