Cinnamoylbenzene → ethyl 2-[(E)-3-(1,2,3,4-tetrahydro-1,4a,9b-trimethyl-1,4-methanodibenzofuran-8-yl)-3-oxo-1-propenyl]-4-thiophenecarboxylate

HRID 1289149Notes

Reaction equation

HRID 1289149 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]3([CH3:18])[CH:12]4[CH2:16][C:15]([CH3:17])([C:9]3([CH3:19])[C:8]=2[CH:20]=1)[CH2:14][CH2:13]4)=[O:3].C1(C=CC(C2C=CC=CC=2)=O)C=CC=CC=1.[CH2:37]([O:39][C:40]([C:42]1[CH:43]=[C:44]([CH:47]=O)[S:45][CH:46]=1)=[O:41])[CH3:38]>>[CH3:17][C:15]12[CH2:16][CH:12]([C:10]3([CH3:18])[C:9]1([CH3:19])[C:8]1[CH:20]=[C:4]([C:2](=[O:3])/[CH:1]=[CH:47]/[C:44]4[S:45][CH:46]=[C:42]([C:40]([O:39][CH2:37][CH3:38])=[O:41])[CH:43]=4)[CH:5]=[CH:6][C:7]=1[O:11]3)[CH2:13][CH2:14]2

Participants

4

Reactant 3

HCID 7189CinnamoylbenzeneHCID 153441301,2,3,4-Tetrahydro-1,4a,9b-trimethyl-1,4methanodibenzofuran-8-yl methyl ketoneHCID 18789515Ethyl 5-formylthiophene-3-carboxylate

Product 1

HCID 18925572ethyl 2-[(E)-3-(1,2,3,4-tetrahydro-1,4a,9b-trimethyl-1,4-methanodibenzofuran-8-yl)-3-oxo-1-propenyl]-4-thiophenecarboxylate

Procedure

2.70 g (10 mmol) of the methyl ketone obtained in Example 3 were converted to chalcone in the presence of 1.7 g of 4-(ethoxycarbonyl)thiophenecarbaldehyde under the conditions described in Example 8 to yield, after recrystallization in ethyl acetate, 2.2 g (52%) of the expected compound, melting at 149°-151° C.

Workup

  1. customto yield
  2. customafter recrystallization in ethyl acetate

Sources & evidence

ORD record
ord-8430838696bc4e42921f499721e3f866
Source dataset
uspto-grants-1998_05
Patent number
US05747530

Reaction notes

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