Hydrochloric Acid → HCID 19916968, compound

HRID 1756161Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][O:10][CH2:11][CH2:12][C:13]2[CH:17]=[CH:16][S:15][CH:14]=2)[CH:5]=[CH:6][CH:7]=1.[Cu](C#N)[C:19]#[N:20].O.Cl>CN(C)C=O.[Fe](Cl)Cl>[C:19]([C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][O:10][CH2:11][CH2:12][C:13]2[CH:17]=[CH:16][S:15][CH:14]=2)[CH:5]=[CH:6][CH:7]=1)#[N:20]

Participants

Conditions

Temperature: 150 °C

Procedure

46 mg of the resulting ether compound was dissolved in 1 ml of dimethylformamide, and 17 mg of copper cyanide was added. The mixture was stirred overnight at 150° C. To this solution was added, a mixture of 39 mg of iron(II) chloride, 0.1 ml of water and 16 μl of hydrochloric acid, and the mixture was stirred at 60° C. for 30 minutes. The solution was extracted with ethyl ether, and the extract was worked up in a customary manner to give 17 mg of 3-[2-[2-(3cyanophenyl)ethoxy]ethyl]thiophene as a colorless oil.

Workup

additionTo this solution was added
stirringthe mixture was stirred at 60° C. for 30 minutes
extractionThe solution was extracted with ethyl ether

Sources & evidence

ORD record: ord-6e37a3a4aa0e4453b0e0a56025766dad
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05439932

Reaction notes

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