tert-Butoxy bis(dimethylamino)methane → HCID 11737295, compound

HRID 1751400Notes

Reaction equation

HRID 1751400 reaction equation
C(O[CH:6]([N:10]([CH3:12])[CH3:11])N(C)C)(C)(C)C.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[C:16]([OH:23])[CH:15]=1>C1(C)C=CC=CC=1>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:22])/[CH:21]=[CH:6]/[N:10]([CH3:11])[CH3:12])=[C:16]([OH:23])[CH:15]=1

Participants

4

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 107274031-(4-Bromo-2-hydroxyphenyl)ethan-1-one

Product 1

HCID 11737295HCID 11737295, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-tert-Butoxy-N,N,N′,N′-tetramethylmethanediamine (19.2 mL, 93.0 mmol) and solution of 1-(4-bromo-2-hydroxyphenyl)ethanone (10 g, 46.5 mmol) in toluene (100 mL) was heated at 35° C. for 16 hours and at 80° C. for 1 hour. The solvent was removed under reduced pressure. The resulting solid was subjected to flash chromatography with eluant of dichloromethane. The product containing fractions were combined and the solvent was removed under reduced pressure to provide (E)-1-(4-bromo-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-one (10.4 g, 38.5 mmol, 82%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionThe product containing fractions
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-239362f861f843d697b25c49b54be952
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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