Benzenepropanal → 2-benzyl-4H,9H-naphtho[2,3-b]furan-4,9-dione

HRID 332119Notes

Reaction equation

HRID 332119 reaction equation
[OH:1][C:2]1[C:3](=[O:14])[C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[C:6](Cl)[CH:5]=2.[CH:15](=O)[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH2:17]([C:16]1[O:1][C:2]2[C:3](=[O:14])[C:4]3[C:9]([C:10](=[O:12])[C:11]=2[CH:15]=1)=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH:1][C:2]1[C:3](=[O:14])[C:4]2[C:9]([C:10](=[O:12])[C:11]=1[CH:15]=[CH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 2

HCID 7707BenzenepropanalHCID 178516609HCID 178516609, compound

Product 2

HCID 582601312-benzyl-4H,9H-naphtho[2,3-b]furan-4,9-dioneHCID 178516888HCID 178516888, compound

Procedure

The intermediate product 2-hydroxy-3-(3-phenyl-1-n-propenyl)-1,4-naphthoquinone 1-2 (R1=H, R4=C6H5) was prepared according to the procedure described in example 3 by using 2-hydroxy-1,4-naphthoquinone 1-1 (R1=H) and hydrocinnamaldehyde as starting material. 2-benzyl-4H,9H-naphtho[2,3-b]furan-4,9-dione 1-3 (R1=H, R4=C6H5) was obtained from 10 gram (0.035 mol) of 1-2 (R1=H, R4=C6H5) by using the procedure described in example 4 to afford yellow crystals; 50% yield. 2-benzyl-4H,9H-naphtho[2,3-b]furan-4,9-dione 1-3 (R1=H, R4=C6H5), 1H NMR (in CDCl3) δ 4.14 (s, 2H), 6.56 (s, 1H), 7.27-7.38 (m, 5H), 7.70-7.77 (m, 2H), 8.14-8.22 (m, 2H);

Workup

  1. customThe intermediate product 2-hydroxy-3-(3-phenyl-1-n-propenyl)-1,4-naphthoquinone 1-2 (R1=H, R4=C6H5) was prepared

Sources & evidence

ORD record
ord-a9928c19f9254aee9c2d3b2bbf7aae27
Source dataset
uspto-grants-2014_11
Patent number
US08877803B2

Reaction notes

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