N,N,N-trimethyl-1,1-bis(1-methylethoxy)amine → 5-((E)-3-Dimethylamino-acryloyl)-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 1619080Notes

Reaction equation

HRID 1619080 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11](=[O:13])[CH3:12])[NH:8][CH:7]=1)=[O:5])[CH3:2].C(O[CH:18](OC(C)C)[N:19]([CH3:21])[CH3:20])(C)C.C([O-])(O)=O.[Na+]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11](=[O:13])/[CH:12]=[CH:18]/[N:19]([CH3:21])[CH3:20])[NH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 87682N,N,N-trimethyl-1,1-bis(1-methylethoxy)amineHCID 516892Sodium BicarbonateHCID 584657325-Acetyl-1H-pyrrole-3-carboxylic acid ethyl ester

Product 1

HCID 666782365-((E)-3-Dimethylamino-acryloyl)-1H-pyrrole-3-carboxylic acid ethyl esterYield 72.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 5-Acetyl-1H-pyrrole-3-carboxylic acid ethyl ester (0.560 g, 3.1 mmol) in 5 mL of dimethylformamide, N,N-dimethylformamide diisopropyl acetal (1.9 mL, 9.3 mmol) was added. The mixture was stirred for at 65° C. for 6 hrs. After cooling to room temperature an aqueous solution of NaHCO3 2% (30 mL) was added and extracted with ethyl acetate (50 mL×2). Organic layer was separated and washed with water (10 mL) and brine (10 mL), dried over sodium sulfate, filtered, and concentered in vacuo to give 0.531 g (72%) of the title compound.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate (50 mL×2)
  3. customOrganic layer was separated
  4. washwashed with water (10 mL) and brine (10 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered

Sources & evidence

ORD record
ord-a64a5bd22da1469b9104c48f4706b3e8
Source dataset
uspto-grants-2014_07
Patent number
US08772280B2

Reaction notes

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