2-(Bromomethyl)acrylic acid ethyl ester → HCID 68308792, compound

HRID 2280209Notes

Reaction equation

HRID 2280209 reaction equation
Br[CH2:2][C:3](=[CH2:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:10][NH2:11].CO.[CH2:14]1[O:24][C:17]2([CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]2)[O:16][CH2:15]1>C1(C)C=CC=CC=1>[CH3:10][N:11]1[C:20]2[CH2:21][CH2:22][C:17]3([O:24][CH2:14][CH2:15][O:16]3)[CH2:18][C:19]=2[CH2:9][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:2]1

Participants

5

Reactant 3

HCID 3106202-(Bromomethyl)acrylic acid ethyl esterHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 57454252Monomethylamine methanol

Product 1

HCID 68308792HCID 68308792, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

To a mixture of ethyl 2-(bromomethyl)acrylate (20.42 g) and toluene (320 mL) was added dropwise a mixture of a 40% methylamine-methanol solution (240.1 mL) and toluene (80 mL) under ice cooling while stirring. The mixture was stirred for 3 minutes. To the mixture was added a mixture of 1,4-cyclohexandione monoethylene ketal (14.00 g) and toluene (100 mL) under the same conditions. The mixture was refluxed with the Dean-Stark apparatus for 4.5 hours. After cooling to room temperature, the mixture was passed through a layer of Celite (registered mark). The filtrate was concentrated under reduced pressure. The residue was purified by aminopropyl silica gel column chromatography (eluent: 0%-40% ethyl acetate/hexane, gradient elution) to give the title compound (22.92 g).

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was stirred for 3 minutes
  3. additionTo the mixture was added
  4. temperatureThe mixture was refluxed with the Dean-Stark apparatus for 4.5 hours
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by aminopropyl silica gel column chromatography (eluent: 0%-40% ethyl acetate/hexane, gradient elution)

Sources & evidence

ORD record
ord-088b118421f246a58d76b959cc1cebb3
Source dataset
uspto-grants-2015_09
Patent number
US09138434B2

Reaction notes

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