Malononitrile → Dihydro-2H-pyran-4,4(3H)-dicarbonitrile
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
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
- extractionextracted 3 times with 5% aqueous NaHCO3
- dry with materialThe organic phase was dried over Na2SO4
- customevaporated under reduced pressure
- customThe crude material was purified by flash chromatography
- 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
反応ノート
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