Dimethyl Sulfate → 2-(4-Tert-butyl-3-methoxyphenyl)isoindoline-1,3-dione

HRID 471957Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([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:7][C:6]=1[OH:22])([CH3:4])([CH3:3])[CH3:2].S(OC)(O[CH3:27])(=O)=O.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:12](=[O:21])[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:19]2=[O:20])=[CH:7][C:6]=1[O:22][CH3:27])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2-(4-tert-butyl-3-hydroxy-phenyl)isoindoline-1,3-dione (450 mg, 1.52 mmol), dimethyl sulfate (385 mg, 288 μL, 3.05 mmol), K2CO3 (632 mg, 4.57 mmol) in acetone (10 mL) was stirred at 50° C. for 3 h. The reaction was cooled to room temperature, filtered and washed with acetone (10 mL). The filtrate was concentrated in vacuo and the residue purified by silica gel chromatography (20% ethyl acetate/hexane) to provide 2-(4-tert-butyl-3-methoxyphenyl)isoindoline-1,3-dione (420 mg, 89% yield). 1H NMR (400.0 MHz, CDCl3) δ 7.72 (m, 2H), 7.55 (m, 2H), 7.15 (d, J=8.3 Hz, 1H), 6.72 (dd, J=2.1, 8.2 Hz, 1H), 6.68 (d, J=2.0 Hz, 1H), 3.61 (s, 3H), 1.15 (d, J=3.4 Hz, 9H).

Workup

temperatureThe reaction was cooled to room temperature
filtrationfiltered
washwashed with acetone (10 mL)
concentrationThe filtrate was concentrated in vacuo
customthe residue purified by silica gel chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-add497dfe73848478cd6879b07bb7c32
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633189B2

Reaction notes

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