5-Methoxy-2-(4-methoxy-phenyl)-7-propyl-benzofuran → 2-(4-Hydroxy-phenyl)-7-propyl-benzofuran-5-ol
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]=1Participants
3
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, 1 H), 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, 2 H, 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-ac739cf436fc43dfb2eab80da8ef35b6
- Source dataset
- uspto-grants-2006_04