Ethyl chloroformate → HCID 15023300, compound

HRID 1090726Notes

Reaction equation

HRID 1090726 reaction equation
[CH2:1]([C:15]1[NH:16][CH:17]=[CH:18][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C[Mg]Br.[C:23](Cl)(=[O:27])[O:24][CH2:25][CH3:26].[Cl-].[NH4+]>CCOCC>[CH2:1]([C:15]1[NH:16][C:17]([C:23]([O:24][CH2:25][CH3:26])=[O:27])=[CH:18][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 10928Ethyl chloroformateHCID 25517Ammonium ChlorideHCID 15023251HCID 15023251, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 15023300HCID 15023300, compoundYield 37.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Into 20 ml of anhydrous ether was dissolved 4.00 g (15 mmol) of 2-tetradecylpyrrole obtained in Synthetic Example 2, and then 7 ml (21 mmol) of ca. 3M ethereal solution of methylmagnesium bromide was added thereto at room temerature. The resulting mixture was heated under reflux for 30 minutes. Under cooling with ice water, 2 ml (21 mmol) of ethyl chlorocarbonate was added to the mixture. After heating under reflux for 10 hours, the resulting mixture was cooled to room temperature, poured into ice water containing ammonium chloride, and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous megnesium sulfate. After removing the solvent under reduced pressure, the residue was purified by subjecting it to column chromatography (eluent: ethyl acetate/hexane=1/10) to obtain 1.89 g (37% yield) of ethyl 5-tetradecylpyrrole-2-carboxylate, m.p. 60°-63° C.

Workup

  1. customobtained in Synthetic Example 2
  2. temperatureThe resulting mixture was heated
  3. temperatureunder reflux for 30 minutes
  4. additionwas added to the mixture
  5. temperatureAfter heating
  6. temperatureunder reflux for 10 hours
  7. extractionextracted with ethyl acetate
  8. washThe extract was washed with water
  9. dry with materialdried over anhydrous megnesium sulfate
  10. customAfter removing the solvent under reduced pressure
  11. customthe residue was purified

Sources & evidence

ORD record
ord-6982d665f45b490d9e9375228e071cdc
Source dataset
uspto-grants-1992_01
Patent number
US05082856

Reaction notes

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