Potassium Carbonate → HCID 66696612, 화합물

HRID 1672554노트

반응식

HRID 1672554 반응식
[CH2:1]=[C:2]([C@@H:4]1[CH2:9][CH2:8][C:7]([CH:10]=[O:11])=[CH:6][CH2:5]1)[CH3:3].[N+:12]([CH:14](S(C1C=CC(C)=CC=1)(=O)=O)[CH3:15])#[C-:13].C([O-])([O-])=O.[K+].[K+]>CO>[CH3:15][C:14]1[N:12]=[CH:13][O:11][C:10]=1[C:7]1[CH2:8][CH2:9][C@@H:4]([C:2]([CH3:3])=[CH2:1])[CH2:5][CH:6]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 1548901(R)-(+)-PerillaldehydeHCID 110528851-(1-Isocyanoethanesulfonyl)-4-methylbenzene

생성물 1

HCID 66696612HCID 66696612, 화합물수율 70%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of (R)-4-(prop-1-en-2-yl)cyclohex-1-enecarbaldehyde (0.574 g, 3.82 mmol), 1-(1-isocyanoethylsulfonyl)-4-methylbenzene (0.80 g, 3.82 mmol), and K2CO3 (1.06 g, 7.65 mmol) in MeOH (25 mL) was heated at reflux for 2 h. The reaction mixture was cooled to ambient temperature, concentrated in vacuo, and diluted with EtOAc. The organic solution was washed with water, separated, and concentrated in vacuo. The residue was chromatographed on silica gel with EtOAc/hexanes (0%-35%) to isolate 0.54 g (70%) of the title compound as an oil. 1H NMR (300 MHz, DMSO-d6) δ 8.12 (s, 1H), 6.15-6.06 (m, 1H), 4.74 (s, 2H), 2.47-2.25 (m, 3H), 2.24-2.00 (m, 5H), 1.94-1.82 (m, 1H), 1.74 (s, 3H), 1.59-1.40 (m, 1H). MS (DCI+) m/z 204 (M+H).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. concentrationconcentrated in vacuo
  4. additiondiluted with EtOAc
  5. washThe organic solution was washed with water
  6. customseparated
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on silica gel with EtOAc/hexanes (0%-35%)

출처 및 근거

ORD 기록
ord-dd6f9e35c6af4c6397ac47a28ca12bab
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07998993B2

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