2-Methoxyethanol → 2-(3-(3-(2-Methoxyethoxy)phenyl)propyl)isoindoline-1,3-dione

HRID 74342

Reaction equation

HRID 74342 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[CH:5]=[CH:6][CH:7]=1.[CH3:22][O:23][CH2:24][CH2:25]O>>[CH3:22][O:23][CH2:24][CH2:25][O:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 80192-MethoxyethanolHCID 580275422-[3-(3-Hydroxyphenyl)propyl]isoindole-1,3-dione

Product 1

HCID 673180022-(3-(3-(2-Methoxyethoxy)phenyl)propyl)isoindoline-1,3-dione

Procedure

Mitsunobu reaction of phenol 58 with 2-methoxyethanol gave 2-(3-(3-(2-methoxyethoxy)phenyl)propyl)isoindoline-1,3-dione as a clear oil. Yield (0.225 g, 19%): 1H NMR (400 MHz, DMSO-d6) δ 7.81-7.84 (m, 2H), 7.67-7.72 (m, 2H), 7.10-7.16 (m, 1H), 6.76-6.80 (m, 2H), 6.67-6.72 (m, 1H), 4.07-4.11 (m, 2H), 3.70-3.76 (m, 4H), 3.45 (s, 3H), 2.55 (t, J=7.6 Hz, 2H), 1.98-2.05 (m, 2H).

Sources & evidence

ORD record
ord-f061a5a1441848a6b638a0989748bec5
Source dataset
uspto-grants-2014_09
Patent number
US08829244B2

Linked notes

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