Hydrochloric Acid → HCID 11299135, 화합물

HRID 650322노트

반응식

HRID 650322 반응식
Cl[CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:3]1.C(O[K])(C)(C)C.O.Cl>C(O)(C)(C)C>[C:13]1([C:4]2[CH:3]=[CH:2][CH2:7][CH2:6][C:5]=2[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11482466HCID 11482466, 화합물HCID 178418922HCID 178418922, 화합물

생성물 1

HCID 11299135HCID 11299135, 화합물수율 75.3%

시약·촉매·용매 1

HCID 6386tert-Butanol용매

실험 절차

To a stirred solution of ethyl 4-chloro-2-phenylcyclohex-2-enecarboxylate (110 mg, 0.407 mmol) in tert-BuOH(2 ml), tert-BuOK(93 mg, 0.832 mmol) was added by portion on a water bath. After stirring for 1 hr. at room temperature, water was added to the reaction mixture, and it was acidified with dil. HCl aq. and extracted with AcOEt. The organic layer was washed with brine and dried over MgSO4. After removal of the solvent, the residue was purified by column chromatography on silica gel with n-hexane-AcOEt to afford 70 mg of ethyl 2-phenylcyclohexa-1,3-dienecarboxylate (y=74.0%) as a pale yellow oil. 1H-NMR(ppm, 300 MHz, CDCl3) δ 7.14-7.39(5H, m), 6.03-6.24(2H, m), 3.94(2H, q, J=6.9 Hz), 2.55-2.65(2H, m), 2.26-2.35(2H, m), 0.90(3H, t, J=6.9 Hz)

후처리

  1. extractionextracted with AcOEt
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. customAfter removal of the solvent
  5. customthe residue was purified by column chromatography on silica gel with n-hexane-AcOEt

출처 및 근거

ORD 기록
ord-50bb9c09556f4607a4b15de2f190392f
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06271418B1

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