3-Phenylprop-2-Enal → HCID 86761424, 화합물

HRID 1661520노트

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HRID 1661520 반응식
[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

참가 물질

8

반응물 4

HCID 3073-Phenylprop-2-EnalHCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 57545162HCID 57545162, 화합물

생성물 2

HCID 57545213HCID 57545213, 화합물HCID 86761424HCID 86761424, 화합물수율 42.5%

시약·촉매·용매 2

HCID 887Methanol용매HCID 1140Toluene용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1511beca22ad45e9accab8365b937496
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030347B2

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