Hydrochloric Acid → 1-(4-Acetylphenyl)cyclobutanecarbonitrile

HRID 603144노트

반응식

HRID 603144 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]#[N:13])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C([Li])CCC.CON(C)[C:22](=[O:24])[CH3:23].Cl>C1COCC1.[Cl-].[Na+].O>[C:22]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]#[N:13])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1)(=[O:24])[CH3:23]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 537505N-Methoxy-N-methylacetamideHCID 201116081-(4-Bromophenyl)cyclobutanecarbonitrileHCID 178418339Butyllithium

생성물 1

HCID 582984821-(4-Acetylphenyl)cyclobutanecarbonitrile수율 57%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

실험 절차

To a stirred solution of 1-(4-bromophenyl)cyclobutanecarbonitrile (2.8 g, 11.9 mmol) in anhydrous THF (70 mL) at −78° C. is added n-butyllithium (2 M in c-hexane) (7.44 mL, 14.9 mmol). The reaction mixture is stirred at that temperature 10 min., then N-methoxy-N-methyl-acetamide (2.50 mL, 23.8 mmol) is added and the solution is then left to warm-up to room temperature over 1 h. A mixture of brine (30 mL) and 1 N HCl (15 mL) is then slowly added and the solution is extracted with EtOAc (3×100 mL). The organic layer is dried over MgSO4, filtered and concentrated under reduced pressure. The crude product is purified by flash chromatography using a 0 to 20% EtOAc in hexane gradient to yield 1-(4-acetylphenyl)cyclobutanecarbonitrile (1.35 g, 57%) as a yellowish oil. 1H NMR (300 MHz, CHLOROFORM-D) δ 8.03-(2H, m), 7.56-7.50 (2H, m), 2.94-2.81 (2H, m), 2.71-2.57 (2H, m), 2.62 (3H, s), 2.57-2.40 (1H, m), 2.18-2.05 (1H, m).

후처리

  1. waitthe solution is then left
  2. additionis then slowly added
  3. extractionthe solution is extracted with EtOAc (3×100 mL)
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product is purified by flash chromatography

출처 및 근거

ORD 기록
ord-5e6dea93eb584fe1bf31ea1c6f92dd59
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906654B2

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