Potassium Carbonate → HCID 66696612、化合物

HRID 1672554ノート

反応式

HRID 1672554 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 66696612HCID 66696612、化合物収率 70%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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%)

出典と根拠

ORDレコード
ord-dd6f9e35c6af4c6397ac47a28ca12bab
出典データセット
uspto-grants-2011_08
特許番号
US07998993B2

反応ノート

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