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

HRID 1661520Notes

Reaction equation

HRID 1661520 reaction equation
[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

Participants

8

Reactant 4

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

Product 2

HCID 57545213HCID 57545213, compoundHCID 86761424HCID 86761424, compoundYield 42.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1511beca22ad45e9accab8365b937496
Source dataset
uspto-grants-2011_10
Patent number
US08030347B2

Reaction notes

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