Ethanol → 3-[3-(4-Trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-on-4-yl]propionaldehyde

HRID 1880686Notes

Reaction equation

HRID 1880686 reaction equation
C(O)C.[F:4][C:5]([F:19])([F:18])[C:6]1[CH:11]=[CH:10][N:9]=[C:8]([C:12]2[NH:13][O:14][C:15](=[O:17])[N:16]=2)[CH:7]=1.[CH:20]([CH:22]=[CH2:23])=[O:21]>C(N(CC)CC)C>[F:19][C:5]([F:4])([F:18])[C:6]1[CH:11]=[CH:10][N:9]=[C:8]([C:12]2[N:16]([CH2:23][CH2:22][CH:20]=[O:21])[C:15](=[O:17])[O:14][N:13]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 7847AcroleinHCID 178517507HCID 178517507, compound

Product 1

HCID 595703263-[3-(4-Trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-on-4-yl]propionaldehydeYield 64.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 1 ml of ethanol were added 0.12 g of triethylamine, 0.2 g of 3-(4-trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-one, and 0.05 g of acrolein, the mixture was stirred at room temperature for 18 hours, and concentrated, and the residue was subjected to silica gel column chromatography to obtain 0.16 g of 3-[3-(4-trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-on-4-yl]propionaldehyde (present compound (22)).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-ea7216f50cd14a6d979c201c0eccdd26
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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