Triethylamine → HCID 53904285, compound

HRID 1107793Notes

Reaction equation

HRID 1107793 reaction equation
[CH2:1]([NH:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:2]=[CH:3][CH3:4].Cl[C:13]([CH2:18][CH3:19])=[C:14]([CH3:17])[CH:15]=O.C(N(CC)CC)C.CC(C)([O-])C.[K+].[Cl-].[NH4+]>C(O)C>[CH2:1]([N:5]1[C:13]([CH2:18][CH3:19])=[C:14]([CH3:17])[CH:15]=[C:6]1[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:2]=[CH:3][CH3:4]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 5832693-chloro-2-methyl-2-pentenalHCID 23665647Potassium tert-butoxideHCID 53851665HCID 53851665, compound

Product 1

HCID 53904285HCID 53904285, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.74 g (0.024 mole) of ethyl N-(2-butenyl)glycinate were added to a solution of 5.0 g (0.038 mole) of 3-chloro-2-methyl-2-pentenal in 10 ml of ethanol with stirring, and subsequently 6 ml (0.043 mole) of triethylamine were added thereto and stirred at room temperature for 7 hours. After the precipitates deposited were filtered off, 5.35 g (0.048 mole) of potassium tert-butoxide were added to the filtrate by portions and the mixture was stirred for 30 minutes. The reaction mixture was poured into about 150 ml of a saturated aqueous solution of ammonium chloride and extracted with ethyl acetate (once with 100 ml and twice with 50 ml). The combined extracts were washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was purified by column chromatography through silica gel using a 3:97 mixture of ethyl acetate and hexane as an eluent to give 1.53 g of ethyl 1-(2-butenyl)-5-ethyl-4-methylpyrrole-2-carboxylate (cis/trans=76/24) as an orange oil.

Workup

  1. stirringstirred at room temperature for 7 hours
  2. filtrationAfter the precipitates deposited were filtered off
  3. stirringthe mixture was stirred for 30 minutes
  4. extractionextracted with ethyl acetate (once with 100 ml
  5. washThe combined extracts were washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off
  8. customThe residue was purified by column chromatography through silica gel using
  9. additiona 3:97 mixture of ethyl acetate and hexane as an eluent

Sources & evidence

ORD record
ord-80bcda634da64577800b11f9703003a1
Source dataset
uspto-grants-2000_05
Patent number
US06063782

Reaction notes

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