ChemicalBook CAS DataBase List BENZYL PROPARGYL ETHER

BENZYL PROPARGYL ETHER synthesis

10synthesis methods

Product Name:BENZYL PROPARGYL ETHER
CAS Number:4039-82-1
Molecular formula:C10H10O
Molecular Weight:146.19

14593-43-2
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4039-82-1
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Yield: 96%

Reaction Conditions:

Stage #1:benzyl allyl ether with pyridinium perbromide hydrobromide in acetonitrile at 20; for 12 h;Molecular sieve;Inert atmosphere;
Stage #2: with tetra(n-butyl)ammonium hydroxide;dimethyl sulfoxide;triethylamine in water;acetonitrile at 0 - 60; for 2 h;Molecular sieve;Inert atmosphere;Reagent/catalyst;

Steps:

One-Pot Synthesis of 4 by Method B; General Procedure
General procedure: A mixture of allyl alcohol derivative 1 (x g, 1.0 equiv), py·HBr3 (1.1equiv), and MS 13X (ca. 10x g) in MeCN (y mL, 0.1 M) was stirred at r.t. for 12-14 h. Then, DMSO (7y mL), TBAOH (3.1 equiv, 40% in H₂O),and Et₃N (1.1 equiv) were added to the reaction mixture at 0 °C and the system was heated to 60 °C. The reaction was quenched with sat.aq NH₄Cl at 0 °C. After the removal of MS 13X through a cotton filter, the resulting filtrate was extracted with hexane-EtOAc (2:1, 3 × 30mL) and dried (MgSO₄). The combined extracts were concentrated under reduced pressure, and the residue was purified by column chromatography (silica gel) to afford the propargyl alcohol derivative 4.

References:

Kutsumura, Noriki;Inagaki, Mai;Kiriseko, Akito;Saito, Takao [Synthesis,2015,vol. 47,# 13,art. no. SS-2015-F0081-OP,p. 1844 - 1850]