Triphenylphosphine → 4-methoxy-2-oxo-1-(tetrahydro-2H-thiopyran-4-yl)-1,2-dihydropyridine-3-carbonitrile

HRID 1526380ノート

反応式

HRID 1526380 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][NH:6][C:5](=[O:9])[C:4]=1[C:10]#[N:11].[S:12]1[CH2:17][CH2:16][CH:15](O)[CH2:14][CH2:13]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(=O)([O-])O.[Na+].O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]([CH:15]2[CH2:16][CH2:17][S:12][CH2:13][CH2:14]2)[C:5](=[O:9])[C:4]=1[C:10]#[N:11]

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 576296Tetrahydro-2H-thiopyran-4-olHCID 27867023-Pyridinecarbonitrile, 1,2-dihydro-4-methoxy-2-oxo-

生成物 1

HCID 1177702324-methoxy-2-oxo-1-(tetrahydro-2H-thiopyran-4-yl)-1,2-dihydropyridine-3-carbonitrile収率 19.2%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a mixture of 4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile (1.00 g), tetrahydro-2H-thiopyran-4-ol (1.18 g), triphenylphosphine (2.62 g) and tetrahydrofuran (30 mL) was added dropwise diisopropyl azodicarboxylate (2.02 g) at room temperature under nitrogen atmosphere, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted twice with ethyl acetate. The extracts were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (320 mg).

後処理

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-3ee9519ebdaa45ee82d64eab6a70de62
出典データセット
uspto-grants-2015_07
特許番号
US09085578B2

反応ノート

読み込み中…