1-Ethynyl-4-methoxybenzene → 1-(3,5-Dichlorophenyl)-3-(4-methoxyphenyl)prop-2-yn-1-one

HRID 1669846ノート

反応式

HRID 1669846 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[CH:10])=[CH:5][CH:4]=1.C([Li])CCC.[Cl:16][C:17]1[CH:18]=[C:19]([CH:26]=[C:27]([Cl:29])[CH:28]=1)[C:20](N(OC)C)=[O:21]>C1COCC1>[Cl:16][C:17]1[CH:18]=[C:19]([C:20](=[O:21])[C:10]#[C:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:26]=[C:27]([Cl:29])[CH:28]=1

参加物

5

反応物 3

HCID 2510201-Ethynyl-4-methoxybenzeneHCID 587973333,5-Dichloro-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

生成物 1

HCID 673355111-(3,5-Dichlorophenyl)-3-(4-methoxyphenyl)prop-2-yn-1-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
40 °C

実験手順

To a solution of 4-methoxy-1-ethynyl benzene (0.57 g, 4.27 mmol) in 20 mL of anhydrous THF cooled to −78° C. under a N2 atmosphere was added nButLi (3.2 mL, 5.12 mmol). After 5 minutes a solution of 3,5-dichloro-N-methoxy-N-methylbenzamide (1.0 g, 4.27 mmol) in THF (10 mL) was added to the reaction. The reaction was slowly warmed to 40° C. over 30 minutes and then quenched with saturated NH4Cl solution. The resulting bi-phasic mixture was extracted with EtOAc (3×). The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography using 1:10 ethyl acetate-hexanes to give the title compound as a yellow solid. 1H NMR (CDCl3, 500 MHz): δ 8.09 (d, J=2.0 Hz, 2H), 7.7 (d, J=7.1 Hz, 2H), 7.64 (t, J=1.8 Hz, 1H), 7.0 (d, J=8.7 Hz, 1H), 3.91 (s, 3H).

後処理

  1. customquenched with saturated NH4Cl solution
  2. extractionThe resulting bi-phasic mixture was extracted with EtOAc (3×)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-76c5ac48954e45299baa39ea9f3f90f8
出典データセット
uspto-grants-2011_08
特許番号
US07989475B2

反応ノート

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