Pyridine → HCID 53963170, compound

HRID 1578811Notes

Reaction equation

HRID 1578811 reaction equation
N1C=CC=CC=1.[CH3:7][CH:8]([CH2:17][CH2:18][CH:19]=[C:20]([CH3:27])[CH2:21][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])[CH:9]([OH:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].O=[Cr](=O)(O[Cr](=O)([O-])=O)[O-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>O.[O-2].[O-2].[O-2].[Cr+6]>[CH3:7][CH:8]([CH2:17][CH2:18][CH:19]=[C:20]([CH3:27])[CH2:21][CH2:22][CH:23]=[C:24]([CH3:25])[CH3:26])[C:9](=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

6

Reactant 3

HCID 1049Pyridine2×HCID 2724130Cornforth reagentHCID 54045506HCID 54045506, compound

Product 1

HCID 53963170HCID 53963170, compoundYield 57.2%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 962WaterSolvent

Procedure

To a mixture of pyridine (132 ml) and ethyl 3,7,11-trimethyl-6,10-dodecadien-2-ol-1-carboxylate (132 g), the Cornforth reagent (prepared by adding dropwise a solution of chromium trioxide (223 g) in water (150 ml) to pyridine (2230 ml) while cooling with ice water) is added, and the resultant mixture is allowed to stand at room temperature. After removal of the precipitate by filtration, the reaction mixture is admixed with water and extracted with ether. The ether extract is washed with water, dried and evaporated. The residual material is distilled under reduced pressure to give ethyl 3,7,11-trimethyl-6,10-dodecadien-2-one-1-carboxylate (75 g) as a pale yellow oil. B.P. 125° to 129°C/0.06 mmHg. IR: 1740, 1225 cm-1 (COO); 1710 cm-1 (C=O). NMR (carbon tetrachloride): δ 1.25 (m), 1.61 (s), 1.69 (s), 1.98 (s), 2.0-2.8 (m), 3.33 (s), 4.15 (m), 4.8-5.25 (m).

Workup

  1. additionis added
  2. customto stand at room temperature
  3. customAfter removal of the precipitate
  4. filtrationby filtration
  5. extractionextracted with ether
  6. extractionThe ether extract
  7. washis washed with water
  8. customdried
  9. customevaporated
  10. distillationThe residual material is distilled under reduced pressure

Sources & evidence

ORD record
ord-fe941b061dce42b0887bb4812954c8cd
Source dataset
uspto-grants-1976_02
Patent number
US03939202

Reaction notes

Loading…