Hydrochloric Acid → 3-Cyclobutyl-3-oxopropanenitrile

HRID 1914858ノート

反応式

HRID 1914858 の反応式
[H-].[Na+].[CH:3]1([C:7]([O-:9])=O)[CH2:6][CH2:5][CH2:4]1.[C:10](#[N:12])[CH3:11].Cl>C1COCC1.O>[CH:3]1([C:7](=[O:9])[CH2:11][C:10]#[N:12])[CH2:4][CH2:5][CH2:6]1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 6993960Cyclobutanecarboxylate

生成物 1

HCID 138611153-Cyclobutyl-3-oxopropanenitrile

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A 50 mL three necked round bottom flask containing NaH (980 mg, 60%, 24.50 mmol, 1.57 eq.) and THF (10 mL) was heated to reflux under nitrogen for about 30 min. Then a mixture of cyclobutanecarboxylate [CCLXVII] (2 g, 15.6 mmol, 1.00 eq.) and acetonitrile (1 g, 24.3 mmol, 1.56 eq.) in 20 mL of THF was added dropwise to the refluxing suspension. After addition, the resulting mixture was refluxed for 16 h and worked up with water. The pH value of the reaction solution was adjusted to 4 with aqueous HCl solution and extracted with ethyl acetate. The combined organic phases were dried and concentrated, the residue was applied onto a silica gel column with ethyl acetate/petroleum ether as the eluent to give Compound [CCLXVIII] as a yellow oil: 1H NMR (300 MHz, CDCl3) δ ppm 3.40-3.60 (m, 1H), 3.43 (s, 2H), 2.25-2.36 (m, 4H), 2.01-2.15 (m, 1H), 1.82-1.96 (m, 1H).

後処理

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen for about 30 min
  3. additionwas added dropwise to the refluxing suspension
  4. additionAfter addition
  5. temperaturethe resulting mixture was refluxed for 16 h
  6. extractionextracted with ethyl acetate
  7. customThe combined organic phases were dried
  8. concentrationconcentrated
  9. customto give Compound [CCLXVIII] as a yellow oil

出典と根拠

ORDレコード
ord-71b0809b337a4e69b3510110bca5c67b
出典データセット
uspto-grants-2013_12
特許番号
US08614221B2

反応ノート

読み込み中…