反応 #52345

反応方程式

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

収率 72.0%

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

収率 72.0%

溶媒

diethyl ether

triethyl amine

反応条件

後処理

1. 1
   その他sparged with argon for 5 minutes
2. 2
   ろ過filtered over a bed of celite
3. 3
   その他The filtrate was evaporated in vacuo to a brown oil that

実験手順

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.

出典