ChemicalBook CAS DataBase List 5-phenylpenta-2,4-dienal

5-phenylpenta-2,4-dienal synthesis

10synthesis methods

Product Name:5-phenylpenta-2,4-dienal
CAS Number:13466-40-5
Molecular formula:C11H10O
Molecular Weight:158.1965

1-Penten-4-yn-3-ol, 1-phenyl-, 3-acetate, (1E)-

193685-91-5
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13466-40-5
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Yield:13466-40-5 35%

Reaction Conditions:

with methyl trifluoromethanesulfonate in 2,2,2-trifluoroethanol at 70; for 1 h;

Steps:

Methyl Triflate Catalyzed Meyer-Schuster Rearrangement; Cinnamaldehyde (2a); Typical Procedure

General procedure: To a 25 mL round-bottomed flask were added 1-phenylprop-2-yn-1-ol (1a; 40 mg, 0.3 mmol), TFE (0.5 mL), and MeOTf (6 μL, 0.06 mmol, 0.2 equiv). Then the flask was immersed in a 70 °C preheated oil bathand the mixture was stirred for 1 h. After completion, the solution was removed and the residue was subject to flash chromatography (silica gel) with PE/EtOAc as eluent to afford the desired rearrangement product.

References:

Yang, Lu;Zeng, Qingle [Synthesis,2017,vol. 49,# 14,p. 3149 - 3156]

58506-33-5 Synthesis