Methylamine → dihydro-2,2,5,5-tetramethyl-4-methylaminomethylene-3(2H)furanone

HRID 1195631Notes

Reaction equation

HRID 1195631 reaction equation
[CH3:1][NH2:2].O[CH:4]=[C:5]1[C:9]([CH3:11])([CH3:10])[O:8][C:7]([CH3:13])([CH3:12])[C:6]1=[O:14]>C(Cl)(Cl)Cl>[CH3:12][C:7]1([CH3:13])[C:6](=[O:14])[C:5](=[CH:4][NH:2][CH3:1])[C:9]([CH3:11])([CH3:10])[O:8]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 675748794-hydroxymethylene-dihydro-2,2,5,5-tetramethyl-3(2H)-furanone

Product 1

HCID 53987429dihydro-2,2,5,5-tetramethyl-4-methylaminomethylene-3(2H)furanoneYield 74%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Methylamine gas was bubbled through a solution of 4-hydroxymethylene-dihydro-2,2,5,5-tetramethyl-3(2H)furanone (5.0 g, 29 mmol) in 50 mL of chloroform for 30 min. The solvents were evaporated. The solid residue was recrystallized from hexanes to give 4.0 g (74%) of dihydro-2,2,5,5-tetramethyl-4-methylaminomethylene-3(2H)furanone as a light yellow solid: mp 80°-82° C.; Anal Calc'd for C10H17NO2 : C, 65.57; H, 9.29; N, 7.65. Found: C, 65.47; H, 9.30; N, 7.60.

Workup

  1. customThe solvents were evaporated
  2. customThe solid residue was recrystallized from hexanes

Sources & evidence

ORD record
ord-3ee0b4fd91a6471c9b84bfb305203f82
Source dataset
uspto-grants-1992_05
Patent number
US05112595

Reaction notes

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