4-Chlorobenzyl alcohol → 2-(3-(3-(4-Chlorobenzyloxy)phenyl)propyl)isoindoline-1,3-dione

HRID 74390

Reaction equation

HRID 74390 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.[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]O)=[CH:25][CH:24]=1>>[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][O:1][C:2]2[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][N:11]3[C:19](=[O:20])[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12]3=[O:21])[CH:5]=[CH:6][CH:7]=2)=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 133974-Chlorobenzyl alcoholHCID 580275422-[3-(3-Hydroxyphenyl)propyl]isoindole-1,3-dione

Product 1

HCID 673167092-(3-(3-(4-Chlorobenzyloxy)phenyl)propyl)isoindoline-1,3-dione

Procedure

Mitsunobu coupling of phenol 58 with 4-chlorobenzylalcohol followed by flash chromatography (5 to 30% EtOAc-hexanes gradient) gave 2-(3-(3-(4-chlorobenzyloxy)phenyl)propyl)isoindoline-1,3-dione as a colorless oil. Yield (2.82 g, 71%). 1H NMR (400 MHz, CDCl3) δ 7.79-7.82 (m, 2H), 7.67-7.69 (m, 2H), 7.31-7.38 (m, 4H), 7.15 (t, J=8.0 Hz, 1H), 6.79-6.81 (m, 2H), 6.70-6.73 (m, 1H), 4.99 (s, 2H), 3.72 (t, J=7.2 Hz, 2H), 2.65 (t, J=8.0 Hz, 2H), 2.02 (dddd, J=7.2 Hz, 2H).

Sources & evidence

ORD record
ord-d6c26d4809f649be88267719a89f7821
Source dataset
uspto-grants-2014_09
Patent number
US08829244B2

Linked notes

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