Sulfuric Acid → (E)-3-(3-thienyl)cinnamaldehyde

HRID 1464760Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=2)/[CH:9]=[CH:10]/[C:11]#N)=[CH:2]1.[H-].C([Al+]CC(C)C)C(C)C.S(=O)(=O)(O)[OH:27]>C1(C)C=CC=CC=1>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=2)/[CH:9]=[CH:10]/[CH:11]=[O:27])=[CH:2]1

Participants

Conditions

Temperature: -78 °C

Procedure

0.4 g of the resulting nitrile compound was dissolved in 2 ml of toluene, and under cooling at -78° C., a 1.0M toluene solution(2 ml) of diisobutylaluminum hydride was added. The mixture was stirred at this temperature for 20 minutes, and then poured into ice-cold water. The resulting solution was acidified with a small amount of a 10% aqueous solution of sulfuric acid, and extracted with ethyl ether. The extract was worked up in a customary manner, and purified by medium-pressure liquid chromatography [silica gel column, hexane/ethyl acetate=9/1→7/1] to give 0.2 g of the captioned compound as a pale yellow oil.

Workup

additionpoured into ice-cold water
extractionextracted with ethyl ether
custompurified by medium-pressure liquid chromatography [silica gel column, hexane/ethyl acetate=9/1→7/1]

Sources & evidence

ORD record: ord-73d1b34cdb4d416db844a9c436294b5f
Source dataset: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05306728

Reaction notes

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