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ChemicalBook CAS DataBase List 1-PHENYL-2-PROPYN-1-OL

1-PHENYL-2-PROPYN-1-OL synthesis

12synthesis methods
-

Yield:4187-87-5 100%

Reaction Conditions:

in tetrahydrofuran at 0 - 20; for 20 h;Inert atmosphere;Schlenk technique;

Steps:

1-phenylprop-2-yn-1-ol 7
A solution of benzaldehyde (2.0 mL, 19.7 mmol) in distilled THF (10 mL) was treated at 0°C with ethynylmagnesium bromide (51 mL, 59.1 mmol). The resulting mixture was stirredat 0 °C for 1 h and for 19 h at r.t.. After treatment with a saturated aqueous solution of NH4Cl and extractionswith Et2O, the combined organic layers were washed with brine, dried over MgSO4 and concentrated underreduced pressure. Purification by silica gel chromatography (pentane/EtOAc: 95/5) afforded the expectedpropargyl alcohol 7 as a pale yellow powder (2.60 g, 19.7 mmol, quantitative yield).

References:

Cocq, Kévin;Saffon-Merceron, Nathalie;Poater, Albert;Maraval, Valérie;Chauvin, Remi [Synlett,2016,vol. 27,# 14,art. no. ST-2016-W0336-C,p. 2105 - 2112] Location in patent:supporting information

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