tert-Butoxy bis(dimethylamino)methane → HCID 68783613, compound

HRID 2264394Notes

Reaction equation

HRID 2264394 reaction equation
[CH3:1][C:2]1([CH3:10])[C:6](=[O:7])[CH2:5][C:4]([CH3:9])([CH3:8])[O:3]1.C(O[CH:16](N(C)C)[N:17]([CH3:19])[CH3:18])(C)(C)C>>[CH3:16][N:17]([CH:19]=[C:5]1[C:4]([CH3:9])([CH3:8])[O:3][C:2]([CH3:10])([CH3:1])[C:6]1=[O:7])[CH3:18]

Participants

3

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 1385112,2,5,5-Tetramethyltetrahydro-3-ketofuran

Product 1

HCID 68783613HCID 68783613, compoundYield 84%

Conditions

Temperature
60 °C

Procedure

A mixture of 2,2,5,5-tetramethyl-dihydro-furan-3-one (2.84 g, 20.0 mmol, 1.0 equiv; commercially available) and tert-butoxy-bis(dimethylamino)methane (3.65 g, 20.9 mmol, 1.05 equiv; commercially available) was heated to 60° C. for 24 h (in analogy to a procedure described in H. H. Wasserman and J. L. Ives J. Am. Chem. Soc. 1976, 98, 7868-7869). The residue was purified by flash column chromatography on silica eluting with diethyl ether to yield 3.3 g (84% yield) of the title compound. MS (EI): 197 [M]+.

Workup

  1. customThe residue was purified by flash column chromatography on silica eluting with diethyl ether

Sources & evidence

ORD record
ord-2bee6c6b4750487c94872c134777a154
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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