3-(benzyloxy)propyl Methanesulfonate → 2-(3-(3-(3-(Benzyloxy)propoxy)phenyl)propyl)isoindoline-1,3-dione

HRID 74376Notes

Reaction equation

HRID 74376 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.[CH2:22]([O:29][CH2:30][CH2:31][CH2:32]OS(C)(=O)=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH2:22]([O:29][CH2:30][CH2:31][CH2:32][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)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 137098283-(benzyloxy)propyl MethanesulfonateHCID 580275422-[3-(3-Hydroxyphenyl)propyl]isoindole-1,3-dione

Product 1

HCID 673171322-(3-(3-(3-(Benzyloxy)propoxy)phenyl)propyl)isoindoline-1,3-dione

Procedure

Alkylation reaction of phenol 58 with methane sulfonic acid 3-benzyloxy-propyl ester gave 2-(3-(3-(3-(benzyloxy)propoxy)phenyl)propyl)isoindoline-1,3-dione as yellow oil. Yield (0.643 g, 44%): 1H NMR (400 MHz, DMSO-d6) δ 7.80-7.83 (m, 2H), 7.68-7.72 (m, 2H), 7.27-7.35 (m, 5H), 7.12-7.16 (m, 1H), 6.77 (d, J=7.6, 1H), 6.73 (s, 1H), 6.66 (d, J=8.0, 1H), 4.53 (s, 2H), 4.06 (t, J=6.0 Hz, 2H), 3.77 (t, J=6.2 Hz, 2H), 3.68 (t, J=5.0 Hz, 2H), 2.65 (t, J=7.8 Hz, 2H), 2.0-2.10 (m, 4H).

Sources & evidence

ORD record
ord-011e21c420eb40a091a15e834ce4126e
Source dataset
uspto-grants-2014_09
Patent number
US08829244B2

Reaction notes

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