1-Butanol, 4-methoxy- → Phthalimide

HRID 875516

Reaction equation

HRID 875516 reaction equation
OC1C=C(CCC[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])C=CC=1.COCCCCO>>[C:12]1(=[O:21])[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:19](=[O:20])[NH:11]1

Participants

3

Reactant 2

HCID 81071-Butanol, 4-methoxy-HCID 580275422-[3-(3-Hydroxyphenyl)propyl]isoindole-1,3-dione

Product 1

HCID 6809Phthalimide

Procedure

Mitsunobu reaction of phenol 58 with 4-methoxybutanol gave 2434344-methoxybutoxy)phenyl)propyl)isoindoline-1,3-dione as yellow oil. Yield (0.840 g, 66%): 1H NMR (400 MHz, CDCl3) δ 7.80-7.85 (m, 2H), 7.68-7.72 (m, 2H), 7.11-7.17 (m, 1H), 6.72-6.79 (m, 2H), 6.65 (dd, J=8.2, 2.4 Hz, 1H), 3.95 (t, J=6.2 Hz, 2H), 3.75 (t, J=6.8 Hz, 2H), 3.44 (t, J=6.4 Hz, 2H), 3.35 (s, 3H), 2.65 (t, J=7.2 Hz, 2H), 1.98-2.06 (m, 2H), 1.70-1.86 (m, 4H).

Sources & evidence

ORD record
ord-384efd2fbec04cdaadeb7a118731d8ab
Source dataset
uspto-grants-2015_03
Patent number
US08981153B2

Linked notes

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