5-Methoxy-2-(4-methoxy-phenyl)-7-propyl-benzofuran → 2-(4-Hydroxy-phenyl)-7-propyl-benzofuran-5-ol

HRID 1835988Notes

Reaction equation

HRID 1835988 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH2:20][CH2:21][CH3:22])[C:6]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=3)=[CH:8][C:7]=2[CH:19]=1.N1C(=O)CC[C@H]1C(O)=O.Cl>>[OH:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[O:10][C:6]3[C:5]([CH2:20][CH2:21][CH3:22])=[CH:4][C:3]([OH:2])=[CH:19][C:7]=3[CH:8]=2)=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 102148975-Methoxy-2-(4-methoxy-phenyl)-7-propyl-benzofuranHCID 67725173Pyr-HCl

Product 1

HCID 101493012-(4-Hydroxy-phenyl)-7-propyl-benzofuran-5-ol

Procedure

Compound 35 was prepared via demethylation of 34 with Pyr-HCl: Mp=178-180° C.; 1H NMR (DMSO-d6) δ 9.81 (br s, 1 H), 9.02 (br s, 1 H), 7.67 (d, 2 H, J=8.5 Hz), 6.98 (s, 1H), 6.87 (d, 2 H, J=8.5 Hz), 6.71 (d, 1 H, J=2.1 Hz), 6.51 (d, 1 H, J=2.1 Hz), 2.84 (t, 2H, J=7.8 Hz), 1.75 (q, 2 H, J=7.4 Hz), 0.96 (t, 3 H, J=7.4 Hz); MS 269 (M+H)+

Sources & evidence

ORD record
ord-11d75671754c4f62877b413324a519f4
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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