Reaction #161538

ord-82055c7ab4a742ccb040dcd005d52371

Reaction equation

O=C1c2ccccc2C(=O)N1CCCc1cccc(O)c1
phenol
O=C1c2ccccc2C(=O)N1CCCc1cccc(O)c1
2-[3-(3-hydroxyphenyl)propyl]isoindole-1,3-dione
BrCC1CCC1
cyclobutylmethyl bromide
O=C1c2ccccc2C(=O)N1CCCc1cccc(OCC2CCC2)c1
2-(3-(3-(cyclobutylmethoxy)phenyl)propyl)isoindoline-1,3-dione

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Alkylation reaction of phenol 58 with cyclobutylmethyl bromide gave 2-(3-(3-(cyclobutylmethoxy)phenyl)propyl)isoindoline-1,3-dione as yellow oil. Yield (0.430 g, 34%): 1H NMR (400 MHz, CDCl3) δ 7.82-7.84 (m, 2H), 7.69-7.71 (m, 2H), 7.11-7.16 (m, 1H), 6.73-6.78 (m, 2H), 6.66 (dd, J=7.6, 2.4 Hz, 1H), 3.88 (d, J=6.4 Hz, 2H), 3.75 (t, J=7.2 Hz, 2H), 2.70-2.79 (m, 1H), 2.66 (t, J=8.0 Hz, 2H), 2.10-2.17 (m, 2H), 2.00-2.07 (m, 2H), 1.82-1.98 (m, 4H).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08829244B2uspto-grants-2014_09