Hydrochloric Acid → 3-Cyclobutyl-3-oxopropanenitrile

HRID 1914858노트

반응식

HRID 1914858 반응식
[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

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 6993960Cyclobutanecarboxylate

생성물 1

HCID 138611153-Cyclobutyl-3-oxopropanenitrile

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-71b0809b337a4e69b3510110bca5c67b
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08614221B2

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