Dichloromethane → 1-(2,4-Dimethoxybenzyl)pyrrolidine-2,5-dione

HRID 853696Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH2:5]O.[NH:13]1[C:17](=[O:18])[CH2:16][CH2:15][C:14]1=[O:19].ClCCl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH2:5][N:13]1[C:17](=[O:18])[CH2:16][CH2:15][C:14]1=[O:19]

Participants

Conditions

Temperature: 0 °C

Procedure

To 2,4-dimethoxybenzyl-alcohol (4.3 g, 25.6 mmol) and pyrrolidine-2,5-dione (succinimide, 1.2 g, 12.2 mmol) dissolved in tetrahydrofuran (25 ml) and dichloromethane (25 ml) was added triphenyphosphine (6.4 g, 24.4 mmol). After cooling to 0° C., diethylazidodicarboxylate (DEAD, 4.25 g, 24.4 mmol) was added dropwise to the reaction mixture. The reaction mixture was then allowed to warm to room temperature and kept at room temperature with stirring overnight. Following concentration in vacuo, 100 ml of a (1:1)hexane/ether solution was added and this mixture was stored at 0° C. overnight. The resulting solid precipitate was filtered off and the filtrate was concentrated in vacuo. The resulting residue was purified by silica gel chromatography (3/1—ethyl acetate/hexane) to afford 1-(2,4-dimethoxy-benzyl)-pyrrolidine-2,5-dione 299 (1.4 g, 5.6 mmol, 46%). 1H NMR (CDCl3) δ 7.07 (d, 1H), 6.38 (m, 2H), 4.60 (s, 2H), 3.76 (s, 3H), 2.62 (s, 4H).

Workup

temperatureto warm to room temperature
customkept at room temperature
concentrationconcentration in vacuo, 100 ml of a (1:1)hexane/ether solution
additionwas added
waitthis mixture was stored at 0° C. overnight
filtrationThe resulting solid precipitate was filtered off
concentrationthe filtrate was concentrated in vacuo
customThe resulting residue was purified by silica gel chromatography (3/1—ethyl acetate/hexane)

Sources & evidence

ORD record: ord-5849d6dc951144df800ea821af2099a6
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253180B2

Reaction notes

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