Carbon Dioxide → HCID 22600909, compound

HRID 2308161Notes

Reaction equation

N(CCO)(CCO)CCO.[CH2:11]([O:21][C:22]1[C:26]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[C:25](C(O)=O)[NH:24][C:23]=1C(O)=O)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C(=O)=O>O>[CH2:11]([O:21][C:22]1[C:26]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:25][NH:24][CH:23]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

Conditions

Temperature: 180 °C

Procedure

Into a 300-ml three-necked flask, 100 ml of triethanolamine was put, and was heated to 180° C. and stirred. Then, 23.4 g (50.0 mmoles) of the 3,4-didecyloxypyrrole-2,5-dicarboxylic acid was added thereto at one time. The mixture was vigorously stirred until carbon dioxide stopped being generated. The reaction product formed was cooled (for about 5 minutes) to room temperature, and 200 ml of water was added thereto, followed by extraction with chloroform. The organic layer formed was dried with magnesium sulfate, and the solvent was evaporated to dryness. The residue was purified by silica gel column chromatography (eluent: chloroform/hexane=2/1) to obtain 17.2 g of 3,4-didecyloxypyrrole (yield: 90.7%).

Workup

customThe reaction product formed
temperaturewas cooled (for about 5 minutes) to room temperature
extractionfollowed by extraction with chloroform
customThe organic layer formed
dry with materialwas dried with magnesium sulfate
customthe solvent was evaporated to dryness
customThe residue was purified by silica gel column chromatography (eluent: chloroform/hexane=2/1)

Sources & evidence

ORD record: ord-69fce75c5e9a4ad09af782954f2426dc
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06835471B2

Reaction notes

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