Ammonia → HCID 19371040, compound

HRID 129329Notes

Reaction equation

HRID 129329 reaction equation
O=[C:2]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:3][CH:4]([CH:10]=O)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH3:26]>>[CH2:12]([C:2]1[NH:26][CH:10]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:3]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 15023379HCID 15023379, compound

Product 1

HCID 19371040HCID 19371040, compoundYield 90%

Procedure

To 4.13 g (12 mmol) of the resulting ethyl γ-keto-α-formyloctadecanoate was added 150 ml of an ammonia-saturated ethanol solution and the mixture was then heated under reflux for 14 hours. After removing the solvent under reduced pressure, the residue was purified by subjecting it to silica gel column chromatography (eluent: ethyl acetate/hexane=1/10) to obtain 3.53 g (90% yield) of ethyl 5-tetradecylpyrrole-3-carboxylate, m.p. 59°-62° C.

Workup

  1. temperaturethe mixture was then heated
  2. temperatureunder reflux for 14 hours
  3. customAfter removing the solvent under reduced pressure
  4. customthe residue was purified

Sources & evidence

ORD record
ord-558f8e88b1f4477f97aaf1132c055fec
Source dataset
uspto-grants-1995_11
Patent number
USRE035096

Reaction notes

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