ChemicalBook CAS DataBase List 1-(2H-1-Benzopyran-3-yl)ethanone

1-(2H-1-Benzopyran-3-yl)ethanone synthesis

5synthesis methods

Product Name:1-(2H-1-Benzopyran-3-yl)ethanone
CAS Number:51593-70-5
Molecular formula:C11H10O2
Molecular Weight:174.2

118-93-4
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78-94-4
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51593-70-5
20 suppliers
$175.00/1g

Yield:51593-70-5 60%

Reaction Conditions:

Stage #1: o-hydroxyacetophenone;methyl vinyl ketonewith potassium carbonate in 1,4-dioxane; for 48 h;Reflux;Inert atmosphere;
Stage #2: Inert atmosphere;

Steps:

General procedure for the synthesis of thesubstrates:1-(2H-chromen-3-yl)propan-1-one (8):

General procedure: To a roundbottom flask charged with amagnetic stirrer was added salicylaldehyde (7.3mmol, 1.27 g), dissolved in 40 mL of 1,4-dioxane. K2CO3 (8.8 mmol, 1.22 g) was thenadded to the solution. Ethyl vinyl ketone (14.7mmol, 1.24 g) was added and the mixture wasleft to reflux for 24 h, followed by the additionof 1.5 eq of ethyl vinyl ketone and reflux foranother 24 h. The reaction was allowed to cooldown to rt and then 1,4-dioxane was removedat reduced pressure. Water and EtOAc wereadded to the flask, and the aqueous layer wasextracted twice with EtOAc. The combinedorganic layers were washed with brine, driedover MgSO4, filtered, and concentrated atreduced pressure to afford 8 in 36% yield as ayellow oil after flash chromatography (SiO2, npentane: EtOAc (95:5)).

References:

Calvo, Beatriz C.;Minnaard, Adriaan J. [Synlett,2017,vol. 28,# 19,p. 2624 - 2628] Location in patent:supporting information

90-02-8 Synthesis