Carbon Dioxide → HCID 22666517, compound

HRID 1007887Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[CH:8]=[CH:9][C:2]1=2.C([Li])CCC.[C:25](=[O:27])=[O:26].Cl>O1CCCC1.CCCCCC.O>[CH2:18]([N:15]([CH2:16][CH3:17])[CH2:14][CH2:13][O:12][CH2:11][CH2:10][C:7]1[CH:8]=[CH:9][C:2]2[S:1][C:5]([C:25]([OH:27])=[O:26])=[CH:4][C:3]=2[CH:6]=1)[CH3:19]

Participants

Conditions

Temperature: -60 °C

Procedure

In 30 mL of tetrahydrofuran is dissolved 6.00 g of N-[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-N,N-diethylamine. The solution is cooled to −60° C., and 10.6 mL of 1.57 mol/L solution of n-butyllithium in hexane is dropwise added. The resulting mixture is stirred at the same temperature as above for one hour, an excessive amount of dry carbon dioxide gas is introduced, after which the temperature is elevated to ambient temperature and the mixture is stirred for 30 minutes. Water is added to the mixture, pH is adjusted to 7 with 2 mol/L hydrochloric acid, and the solvent is distilled off under reduced pressure. The residue is purified by reversed phase column chromatography (eluent:water:methanol=7:3) and filtered together with ethyl acetate. Thus, 3.66 g of 5-{2-[2-(diethylamino)ethoxy]ethyl}-benzo[b]thiophene-2-carboxylic acid is obtained as a crystalline product.

Workup

customis elevated to ambient temperature
stirringthe mixture is stirred for 30 minutes
distillationthe solvent is distilled off under reduced pressure
customThe residue is purified by reversed phase column chromatography (eluent:water:methanol=7:3)
filtrationfiltered together with ethyl acetate

Sources & evidence

ORD record: ord-356384e3ccaa4465bb7bd1a44af3b88d
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06797726B1

Reaction notes

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