Malononitrile → 1,1-Cyclohexanedicarbonitrile

HRID 12481

反応式

HRID 12481 の反応式
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[CH2:6]1[CH2:16][CH2:15]N2C(=NCCC2)[CH2:8][CH2:7]1.BrCCCCCBr>CN(C=O)C>[C:2]1([C:1]#[N:5])([C:3]#[N:4])[CH2:15][CH2:16][CH2:6][CH2:7][CH2:8]1

参加物

5

反応物 3

HCID 8010MalononitrileHCID 81001,5-DibromopentaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

生成物 1

HCID 5445611,1-Cyclohexanedicarbonitrile

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

Malononitril (15.0 g) was dissolved in dry DMF (200 mL). Subsequently, DBU (75 mL) and 1,5-dibromopentane (34 mL) were added at 0° C. (ice bath). The ice bath was removed and the reaction was stirred for 2 h at 80° C. After cooling down, the reaction was poured into DCM. The organic layer was washed several times with 5% NaHCO3, the organic layer dried over Na2SO4 and the solvent evaporated under reduced pressure. The crude product was purified by flash chromatography eluting with PA:EtOAc (9:1) yielding 25.7 g white crystals. 1H NMR (400 MHz, CDCl3) δ 1.48-1.61 (m, 2H), 1.68-1.84 (m, 4H), 2.13 (t, J=6 Hz, 4H).

後処理

  1. customThe ice bath was removed
  2. temperatureAfter cooling down
  3. additionthe reaction was poured into DCM
  4. washThe organic layer was washed several times with 5% NaHCO3
  5. dry with materialthe organic layer dried over Na2SO4
  6. customthe solvent evaporated under reduced pressure
  7. customThe crude product was purified by flash chromatography
  8. washeluting with PA

出典と根拠

ORDレコード
ord-0f24ae48faae41c7bd08e7d80696285f
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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