2-[5-Hydroxy-2-(4-hydroxy-phenyl)-benzofuran-7-yl]-propionitrile → 7-Ethyl-2-(4-hydroxy-phenyl)-benzofuran-5-ol

HRID 1835987Notes

Reaction equation

HRID 1835987 reaction equation
[CH2:1]([C:3]1[C:11]2[O:10][C:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18]C)=[CH:14][CH:13]=3)=[CH:8][C:7]=2[CH:6]=[C:5]([O:20]C)[CH:4]=1)[CH3:2].N1C(=O)CC[C@H]1C(O)=O.Cl.OC1C=C(C(C)C#N)C2OC(C3C=CC(O)=CC=3)=CC=2C=1>>[CH2:1]([C:3]1[C:11]2[O:10][C:9]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)=[CH:8][C:7]=2[CH:6]=[C:5]([OH:20])[CH:4]=1)[CH3:2]

Participants

4

Reactant 3

HCID 101253982-[5-Hydroxy-2-(4-hydroxy-phenyl)-benzofuran-7-yl]-propionitrileHCID 102363677-Ethyl-5-methoxy-2-(4-methoxy-phenyl)-benzofuranHCID 67725173Pyr-HCl

Product 1

HCID 101714797-Ethyl-2-(4-hydroxy-phenyl)-benzofuran-5-ol

Procedure

Compound 30 was prepared by demethylation of 29 using Pyr-HCl (method described previously for preparartion of 21): Mp=218-220° C.; 1H NMR (DMSO-d6) δ 9.81 (s, 1 H), 9.02 (s, 1 H), 7.69 (d, 2 H, J=8.5 Hz), 6.99 (s, 1 H), 6.86 (d, 2 H, J=8.5 Hz), 6.70 (d, 1H, J=2.2 Hz), 6.55 (d, 1 H, J=2.0 Hz), 2.81 (q, 2 H, J=7.5 Hz), 1.29 (t, 3 H, J=7.5 Hz); MS 255 (M+H)+

Sources & evidence

ORD record
ord-f19041de5e8a40c0a012206a464e9700
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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