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Malononitrile → Methyl 3,3-dicyano-2,2-dimethylpropanoate

HRID 400550
ノート
印刷プレビュー

反応式

HRID 400550 の反応式
[C:1](#[N:5])[CH2:2][C:3]#[N:4].CC(C)([O-])C.[K+].Br[C:13]([CH3:19])([CH3:18])[C:14]([O:16][CH3:17])=[O:15]>C1COCC1>[C:3]([CH:2]([C:1]#[N:5])[C:13]([CH3:19])([CH3:18])[C:14]([O:16][CH3:17])=[O:15])#[N:4]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8010MalononitrileHCID 90097Methyl 2-bromo-2-methylpropionateHCID 23665647Potassium tert-butoxide

生成物 1

HCID 86657403Methyl 3,3-dicyano-2,2-dimethylpropanoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

A 12 liter 3 neck round bottom flask equipped with a mechanical stirrer, thermometer, condenser and nitrogen bubbler, was charged with malononitrile (251 g, 3.802 moles) and THF (2 liters). Potassium t-butoxide (1M THF, 3.802 L, 3.802 moles) was then added. The mixture was stirred at 50° C. for 30 min. Methyl 2-bromoisobutyrate (688 g, 3.80 moles) was added and the reaction mixture was stirred overnight at 50° C. The reaction was partitioned between aqueous 1N HCl and EtOAc. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated to give the indicated product. 1H NMR (400 MHz, CD3CN): δ 4.35 (s, 1H); 3.73 (s, 3H); 1.43 (s, 6H).

後処理

  1. stirringthe reaction mixture was stirred overnight at 50° C
  2. customThe reaction was partitioned between aqueous 1N HCl and EtOAc
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the indicated product

出典と根拠

ORDレコード
ord-4c3d11e499284575b969bb24664310e1
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08741910B2

反応ノート

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