Malononitrile → Dihydro-2H-pyran-4,4(3H)-dicarbonitrile

HRID 12506

反応式

HRID 12506 の反応式
[C:1](#[N:5])[CH2:2][C:3]#[N:4].Br[CH2:7][CH2:8][O:9][CH2:10][CH2:11]Br.CC([O-])(C)C.[K+]>CS(C)=O.CCCC[N+](CCCC)(CCCC)CCCC.[Br-].C(Cl)Cl>[O:9]1[CH2:10][CH2:11][C:2]([C:1]#[N:5])([C:3]#[N:4])[CH2:7][CH2:8]1

参加物

7

反応物 3

HCID 8010MalononitrileHCID 21521Bis(2-bromoethyl) etherHCID 23665647Potassium tert-butoxide

生成物 1

HCID 14537194Dihydro-2H-pyran-4,4(3H)-dicarbonitrile収率 24%

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 679Dimethyl Sulfoxide溶媒HCID 6344Dichloromethane溶媒

実験手順

Malononitrile (5.0 g) was dissolved in DMSO (5 mL). Subsequently, bis(2-bromoethyl)ether (9.49 mL) and TBAB (1.22 g) were added, followed by portionwise addition of KOtBu (8.49 g). The mixture was stirred for 4 h. at room temperature, taken up in DCM and extracted 3 times with 5% aqueous NaHCO3. The organic phase was dried over Na2SO4 and evaporated under reduced pressure. The crude material was purified by flash chromatography eluting with PA:Et2O 65:35 (Rf=0.24, visualized with KMnO4) to give 2.49 g (24%) of a solid. 1H NMR (400 MHz, CDCl3) δ 2.24 (t, 4H), 3.87 (t, 4H).

後処理

  1. extractionextracted 3 times with 5% aqueous NaHCO3
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated under reduced pressure
  4. customThe crude material was purified by flash chromatography
  5. washeluting with PA

出典と根拠

ORDレコード
ord-4052a6dbde5847328dbec77949a0b930
出典データセット
uspto-grants-2010_06
特許番号
US07728018B2

関連ノート

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