(2E,4E)-5-PHENYL-PENTA-2,4-DIEN-1-OL synthesis

8synthesis methods

Product Name:(2E,4E)-5-PHENYL-PENTA-2,4-DIEN-1-OL
CAS Number:58506-33-5
Molecular formula:C11H12O
Molecular Weight:160.21

1552-95-0
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58506-33-5
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Yield: 69%

Reaction Conditions:

with diisobutylaluminium hydride in hexane;dichloromethane at -78; for 1.5 h;Inert atmosphere;

Steps:

General procedure A: Reduction of ester
General procedure: To a solution of ester in dry DCM at -78 °C under argon, DIBAL-H (1M solution in hexane) was added dropwise. The resulting mixture was stirred for 1.5 h at -78 °C and then quenched with 10% aqueous solution NaOH. The resulting mixture was warmed to room temperature and stirred for 1 h. The layers were separated and the aqueous layer was extracted with DCM (3 times). The combined organic phases were successively washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude alcohol was purified by flash column chromatography.

References:

Biletskyi, Bohdan;Tenaglia, Alphonse;Clavier, Hervé [Tetrahedron Letters,2018,vol. 59,# 2,p. 103 - 107] Location in patent:supporting information