1-Butyne → HCID 118022026、化合物

HRID 575837ノート

反応式

HRID 575837 の反応式
I[C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[C:4]([I:12])[C:3]=1[OH:13].[CH:14]#[C:15][CH2:16][CH3:17]>N1C=CC=CC=1.Cl>[CH2:16]([C:15]1[O:13][C:3]2[C:4]([I:12])=[CH:5][C:6]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:7][C:2]=2[CH:14]=1)[CH3:17]

参加物

5

反応物 2

HCID 78461-ButyneHCID 49857092,6-Diiodo-4-(methanesulfonyl)phenol

生成物 1

HCID 118022026HCID 118022026、化合物収率 48.4%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 1049Pyridine溶媒

反応条件

温度
130 °C

実験手順

To a solution of 2,6-diiodo-4-methylsulfonylphenol (1.00 g, 2.36 mmol) in pyridine (10 mL) at 25° C. was added but-1-yne (128 mg, 2.36 mmol) and Cu2O (135 mg, 0.944 mmol). The mixture was stirred at 130° C. for 3 h under a nitrogen atmosphere. The residue was cooled to 25° C., diluted with 1N HCl (200 ml) and extracted with EtOAc (30 mL×2). The combined organic layers were washed by brine (100 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography (PE:EA=10:1 to 5:1) to afford the title compound (400 mg, 48%) as a solid. 1H NMR (CDCl3, 400 MHz) δ 8.14 (d, J=1.6 Hz, 1H), 8.06 (d, J=1.6 Hz, 1H), 6.62 (s, 1H), 3.09 (s, 3H), 2.90 (q, J=7.6 Hz, 2H), 1.38 (t, J=7.6 Hz, 3H). LCMS: 350.9 (M+H+)

後処理

  1. temperatureThe residue was cooled to 25° C.
  2. extractionextracted with EtOAc (30 mL×2)
  3. washThe combined organic layers were washed by brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (PE:EA=10:1 to 5:1)

出典と根拠

ORDレコード
ord-975c7111425646ceb92bdee7ba46b225
出典データセット
uspto-grants-2015_05
特許番号
US09034900B2

反応ノート

読み込み中…