Potassium Carbonate → HCID 66696612, compound

HRID 1672554Notes

Reaction equation

HRID 1672554 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 66696612HCID 66696612, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  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%)

Sources & evidence

ORD record
ord-dd6f9e35c6af4c6397ac47a28ca12bab
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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