Iodine → 1-Quinoxalin-2-yl-but-3-yn-1-ol

HRID 334694ノート

反応式

HRID 334694 の反応式
[Mg].II.[CH2:4](Br)[C:5]#[CH:6].[N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][C:9]=1[CH:18]=[O:19].[NH4+].[Cl-]>CCOCC.C1COCC1>[N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][C:9]=1[CH:18]([OH:19])[CH2:6][C:5]#[CH:4]

参加物

8

反応物 5

HCID 807IodineHCID 7842Propargyl bromideHCID 25517Ammonium ChlorideHCID 594088Quinoxaline-2-carbaldehydeHCID 5462224Magnesium

生成物 1

HCID 866302471-Quinoxalin-2-yl-but-3-yn-1-ol収率 14.2%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of magnesium (229 mg, 9.41 mmol), mercuric chloride (13 mg, 47 μmol) and few crystals of iodine in Et2O (1.5 mL), a solution of propargyl bromide (0.53 mL, 5.88 mmol) in Et2O (4.5 mL) was added slowly in order to maintain a reflux. The reaction mixture was stirred 1 hour and added to a solution of quinoxaline-2-carbaldehyde (500 mg, 3.16 mmol) in THF (2 mL). The resulting reaction mixture was stirred at 0° C. for 30 min., at room temperature for 30 min. and was poured onto saturated NH4Cl solution. The aqueous phase was extracted with Et2O. The aqueous phase was washed with water, brine, dried over MgSO4, filtered and evaporated. The crude residue was purified by C18 flash chromatography (H2O/acetonitrile 100:0 to 80:20) to yield 90 mg (0.45 mmol, 14%) of 1-quinoxalin-2-yl-but-3-yn-1-ol as a yellow oil.

後処理

  1. temperatureto maintain a reflux
  2. customThe resulting reaction mixture
  3. stirringwas stirred at 0° C. for 30 min., at room temperature for 30 min.
  4. extractionThe aqueous phase was extracted with Et2O
  5. washThe aqueous phase was washed with water, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude residue was purified by C18 flash chromatography (H2O/acetonitrile 100:0 to 80:20)

出典と根拠

ORDレコード
ord-0f3a9936008745609b7dd2a151345d65
出典データセット
uspto-grants-2014_11
特許番号
US08883826B2

反応ノート

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