Ethyl Acetate → 3-[3-(3-Thienyl)phenoxy] propanal dimethylacetal

HRID 1464769Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=2)=[CH:2]1.[CH3:13][O:14][CH:15]([O:19][CH3:20])[CH2:16][CH2:17]Br.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[CH3:13][O:14][CH:15]([O:19][CH3:20])[CH2:16][CH2:17][O:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)[CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

1.3 g of 3-(3-thienyl)phenol, 1.09 ml of 3-bromopropanal dimethylacetal and 1.1 g of potassium carbonate were dissolved in 10 ml of dimethylformamide, and the mixture was heated at 90° C. with stirring for 6 hours. Ethyl acetate and water were added, and the organic layer separated was worked up in a customary manner, then the product was purified by silica gel column chromatography [hexane / ethyl acetate=30/1→20/1] to give 1.0 g of 3-[3-(3-thienyl)phenoxy] propanal dimethylacetal as a colorless oil.

Workup

customthe organic layer separated
customthe product was purified by silica gel column chromatography [hexane / ethyl acetate=30/1→20/1]

Sources & evidence

ORD record: ord-4c11c325e40045ff9cb39e902e35bc2d
Source dataset: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05306728

Reaction notes

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