反応 #430734

反応方程式

hydrochloric acid

triphenylphosphine

4-(3-cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-ethynylcyclohexane

methyl 3-iodobenzoate

→

4-(3-cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-(3-carbomethoxyphenylethynyl)cyclohexane

溶媒

piperidine

反応条件

後処理

1. 1
   温度The reaction mixture was chilled to 0° C.
2. 2
   抽出was extracted five times with methylene chloride
3. 3
   洗浄The organic phase was washed with dilute hydrochloric acid, water, saturated brine
4. 4
   乾燥was dried over magnesium sulfate
5. 5
   ろ過was filtered
6. 6
   濃縮concentrated in vacuo
7. 7
   その他chromatographed on silica gel
8. 8
   洗浄eluting the with 15 to 20% ethyl acetate in hexanes
9. 9
   その他to afford a light yellow oil

実験手順

A mixture of 4-(3-cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-ethynylcyclohexane (0.150 g, 0.421 mmol) and methyl 3-iodobenzoate (0.110 g, 0.421 mmol) in piperidine (2.1 mL, dry) under an argon atmosphere was treated with a mixture of tetrakis(triphenylphosphine)palladium(0) (0.020 g, 0.017 mmol), cuprous iodide (0.010 g, 0.053 mmol) and triphenylphosphine (crystal) and the mixture was heated at 80° C. for 40 min. The reaction mixture was chilled to 0° C., was poured into ice-water, was acidified with 3N hydrochloric acid and was extracted five times with methylene chloride. The organic phase was washed with dilute hydrochloric acid, water, saturated brine, was dried over magnesium sulfate, was filtered and concentrated in vacuo. The residue was preadsorbed and chromatographed on silica gel, eluting the with 15 to 20% ethyl acetate in hexanes, to afford a light yellow oil. 1H-NMR (250 MHz, CDCl3) δ 8.11 (t, J=1.4 Hz, 1H), 7.97 (d-d, J=1.3 Hz;J=7.9 Hz, 1H), 7.63 (d-d, J=7.8 Hz;J=1.3 Hz, 1H), 7.39 (t, J=7.8 Hz, 1H), 7.23 (d, J=2.2, 1H), 7.15 (d-d, J=8.4 Hz;J=2.3 Hz, 1H), 6.89 (d, J=8.4 Hz, 1H), 4.80 (m, 1H), 4.00 (s, br, 4H), 3.92 (s, 3H), 3.84 (s, 3H), 2.4 to 1.75 (m, 18H).

出典