Ethyl Acetate → 4-(1-Cyanocyclopropyl)benzonitrile

HRID 419945

反応式

HRID 419945 の反応式
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH:11]1([C:14]#[N:15])[CH2:13][CH2:12]1.F[C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=1.C([O-])(O)=O.[Na+].CCOC(C)=O>C1COCC1>[C:14]([C:11]1([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)#[N:15]

参加物

7

反応物 5

HCID 8857Ethyl AcetateHCID 145174-FluorobenzonitrileHCID 79637CyclopropanecarbonitrileHCID 516892Sodium BicarbonateHCID 3251421Potassium bis(trimethylsilyl)amide

生成物 1

HCID 200261814-(1-Cyanocyclopropyl)benzonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-40 °C

実験手順

Solid KHMDS (6.82 g, 34.3 mmol) is dissolved in THF (60.0 mL) and cooled to −40° C. Cyclopropanecarbonitrile (2.30 g, 34.3 mmol) is added, and the resulting solution is stirred for 30 minutes. A solution of 4-fluorobenzonitrile (4.15 g, 34.3 mmol) in THF (20.0 mL) is added, and the mixture is stirred for 20 minutes at −40° C. followed by 2 hours at room temperature. A saturated solution of NaHCO3 (50.0 mL) is added, and the aqueous phase is 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 70% EtOAc) (743 mg, 4.42 mmol, 13%). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.60-1.67 (m, 2H) 1.84-1.90 (m, 2H) 7.49 (d, J=8.59 Hz, 2H) 7.85 (d, J=8.79 Hz, 2H).

後処理

  1. stirringthe mixture is stirred for 20 minutes at −40° C.
  2. waitfollowed by 2 hours at room temperature
  3. extractionthe aqueous phase is extracted with EtOAc (4×40.0 mL)
  4. dry with materialThe combined organic phases are dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated on the rotovaporator
  7. customThe product is purified by flash chromatography (CombiFlash)

出典と根拠

ORDレコード
ord-8c359a63f3e54f36968ea00f3614db67
出典データセット
uspto-grants-2012_01
特許番号
US08093402B2

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