Hydrochloric Acid → HCID 11299135、化合物

HRID 650322ノート

反応式

HRID 650322 の反応式
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

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11482466HCID 11482466、化合物HCID 178418922HCID 178418922、化合物

生成物 1

HCID 11299135HCID 11299135、化合物収率 75.3%

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-50bb9c09556f4607a4b15de2f190392f
出典データセット
uspto-grants-2001_08
特許番号
US06271418B1

反応ノート

読み込み中…