반응 #52345

반응 방정식

6-ethynyl-4,4-dimethyl-1,2,3,4-tetrahydronaphthalene-1-one

Intermediate 13

6-ethynyl-4,4-dimethyl-1,2,3,4-tetrahydronaphthalene-1-one

tetrahydrofuran

→

title compound

수율 72.0%

4-(8,8-Dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalene-2-yl-ethynyl)-benzoic acid ethyl ester

수율 72.0%

용매

diethyl ether

triethyl amine

반응 조건

후처리

1. 1
   기타sparged with argon for 5 minutes
2. 2
   여과filtered over a bed of celite
3. 3
   기타The filtrate was evaporated in vacuo to a brown oil that

실험 절차

A solution of 6-ethynyl-4,4-dimethyl-1,2,3,4-tetrahydronaphthalene-1-one (Intermediate 13, 0.23 g, 1.1 mmol) and ethyl-4-iodo benzoate (Reagent A, 0.36 g, 1.3 mmol) in triethyl amine (7 mL) and anhydrous tetrahydrofuran (3 mL) was treated with copper(I)iodide (0.114 g, 0.6 mmol) and sparged with argon for 5 minutes. Dichlorobis(triphenylphosphine)palladium(II) (0.23 g, 0.33 mmol) was added and the reaction mixture was stirred overnight at room temperature. It was diluted with diethyl ether and filtered over a bed of celite. The filtrate was evaporated in vacuo to a brown oil that was subjected to flash column chromatography over silica gel (230-400 mesh) using 6-7% ethyl acetate in hexane as the eluent to afford the title compound (0.29 g, 72%) as a pale brown solid.

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