3-Bromo-1-propanol → 3-[4-(3-Bromo-propoxy)-2-methoxy-phenyl]-2-methoxy-propionic acid methyl ester

HRID 459279Notes

Reaction equation

HRID 459279 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH:4]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=1[O:15][CH3:16])CC.[Br:18][CH2:19][CH2:20][CH2:21]O.C[CH:24]([O:26]C(/N=N/C(OC(C)C)=O)=O)C.C1(C)C=CC=CC=1>>[CH3:1][O:2][C:3](=[O:17])[CH:4]([O:26][CH3:24])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:21][CH2:20][CH2:19][Br:18])=[CH:10][C:9]=1[O:15][CH3:16]

Participants

4

Reactant 3

HCID 123083-Bromo-1-propanolHCID 694227962-(4-Hydroxy-2-methoxy-benzyl)-butyric acid methyl esterHCID 178459888HCID 178459888, compound

Product 1

HCID 588228803-[4-(3-Bromo-propoxy)-2-methoxy-phenyl]-2-methoxy-propionic acid methyl ester

Procedure

3-(4-Hydroxy-2-methoxy-phenyl)-2-methoxy-propionic acid methyl ester (Example 188, Step C) and 3-bromo-propan-1-ol (Step A) were treated in the standard Mitsunobu conditions B (DIAD/toluene) to afford the title compound. 1H-NMR (CDCl3, 200.15 MHz): δ 7.01 (d, 1H, J=8.3), 6.39 (m, 2H), 4.06 (t, 2H, J=5.9), 4.00–3.96 (m, 1H), 3.78 (s, 3H), 3.67 (s, 3H), 3.57 (t, 2H, J=6.4), 3.31 (s, 3H), 2.99 (dd, 1H, J=13.7, 6.2), 2.91 (dd, 1H, J=13.7, 7.5), 2.34–2.22 (m, 2H).

Sources & evidence

ORD record
ord-cc056eb094f84535a3c212daae3dd73e
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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