Hydrochloric Acid → 4-(1-Cyanocyclobutyl)benzonitrile

HRID 603113

반응식

HRID 603113 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH:11]1([C:15]#[N:16])[CH2:14][CH2:13][CH2:12]1.F[C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1.Cl>C1COCC1>[C:15]([C:11]1([C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=2)[CH2:14][CH2:13][CH2:12]1)#[N:16]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 145174-FluorobenzonitrileHCID 78148CyanocyclobutaneHCID 3251421Potassium bis(trimethylsilyl)amide

생성물 1

HCID 582984874-(1-Cyanocyclobutyl)benzonitrile수율 55.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

Solid KHMDS (3.48 g, 17.5 mmol) is dissolved in THF (20.0 mL) and cooled to 0° C. Cyclobutanecarbonitrile (1.42 g, 17.5 mmol) is added, and the resulting solution stirred for 40 minutes. A solution of 4-fluorobenzonitrile (2.12 g, 17.5 mmol) in THF (10.0 mL) is added, and the mixture stirred for 2 hours at 0° C. 1N HCl (50.0 mL) is added to the reaction mixture and the aqueous phase extracted with EtOAc (4×40.0 mL). The combined organic phases are dried over MgSO4, filtered and concentrated on the rotovaporator. The product is purified by flash chromatography (CombiFlash), eluting with mixtures of heptanes and EtOAc (0% EtOAc to 40% EtOAc) to yield the desired product (1.76 g, 9.67 mmol, 55%). 1H NMR (400 MHz, DMSO-D6) ε ppm 1.92-2.12 (m, 1H) 2.19-2.37 (m, 1H) 2.57-2.69 (m, 2H) 2.71-2.82 (m, 2H) 7.67 (d, J=8.59 Hz, 2H) 7.91 (d, J=8.79 Hz, 2H).

후처리

  1. stirringthe mixture stirred for 2 hours at 0° C
  2. extractionthe aqueous phase extracted with EtOAc (4×40.0 mL)
  3. dry with materialThe combined organic phases are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated on the rotovaporator
  6. customThe product is purified by flash chromatography (CombiFlash)
  7. washeluting with mixtures of heptanes and EtOAc (0% EtOAc to 40% EtOAc)

출처 및 근거

ORD 기록
ord-84ebabcd9ce14158bac68c778d9469e3
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906654B2

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