Sodium hydride → 3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-1-methyl-pyrrolidine-2,5-dione

HRID 247610Notes

Reaction equation

HRID 247610 reaction equation
[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:8]=1[OH:17])([CH3:6])([CH3:5])[CH3:4].[CH3:18][N:19]1[C:23](=[O:24])[CH:22]=[CH:21][C:20]1=[O:25]>C(O)(C)(C)C.C1(C)C=CC=CC=1.CCCCCCC.C(OCC)(=O)C>[C:13]([C:9]1[CH:10]=[C:11]([CH:21]2[CH2:22][C:23](=[O:24])[N:19]([CH3:18])[C:20]2=[O:25])[CH:12]=[C:7]([C:3]([CH3:6])([CH3:5])[CH3:4])[C:8]=1[OH:17])([CH3:16])([CH3:15])[CH3:14]

Participants

8

Reactant 3

HCID 24758Sodium hydrideHCID 314052,6-Di-tert-butylphenolHCID 70261N-Methylmaleimide

Product 1

HCID 141483743-(3,5-Di-tert-butyl-4-hydroxyphenyl)-1-methyl-pyrrolidine-2,5-dioneYield 9.5%

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent2×

Procedure

This compound is prepared by the procedure of Example 1 from 2.40 g (0.1 mol) of sodium hydride, 20.63 g (0.1 mol) of 2,6-di-tert-butylphenol, and 11.11 g (0.1 mol) of N-methylmaleimide in tert-butyl alcohol. The residue is recrystallized from petroleum ether to give 13.2 g (42%) of crude product. The analytical sample is prepared by flash chromatography (1:1 heptane:ethyl acetate eluent) followed by trituration with a mixture of heptane and toluene to give 3.0 g of a white solid: mp 164°-166° C.

Workup

  1. customThe residue is recrystallized from petroleum ether
  2. customto give 13.2 g (42%) of crude product

Sources & evidence

ORD record
ord-53eea7b7a4c14ee1888689b3797f1755
Source dataset
uspto-grants-1987_11
Patent number
US04709050

Reaction notes

Loading…