Pyridine → HCID 21516762, compound

HRID 1283858Notes

Reaction equation

HRID 1283858 reaction equation
N1C=CC=CC=1.[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([CH:22]([OH:24])[CH3:23])[CH:16]([CH2:19][O:20][CH3:21])[CH2:17][OH:18])#[N:8]>[O-2].[O-2].[O-2].[Cr+6].ClCCl>[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([C:22]([CH3:23])=[O:24])[CH:16]([CH2:19][O:20][CH3:21])[CH:17]=[O:18])#[N:8]

Participants

5

Reactant 2

HCID 1049PyridineHCID 21516763HCID 21516763, compound

Product 1

HCID 21516762HCID 21516762, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 1.874 g. of pyridine (dried over barium oxide) and 60 ml. of dichloromethane (dried over calcium chloride) was added in one portion 1.237 g. of chromium trioxide (dried over phosphorus pentoxide). The mixture was stirred at room temperature for 15 mins. then 0.255 g. of 3-(6-cyanohexyl)-2-methoxymethyl-1,4-pentanediol in 5 ml. of dry dichloromethane was added in one portion. The reaction mixture was stirred at room temperature for 0.5 hr., at the end of which the supernatant was decanted into a separatory funnel. The residue was washed several times with diethyl ether (total 150 ml.). The combined organic solutions were washed three times with 20 ml. portions of 5% aqueous potassium hydroxide solution, twice with 20 ml. portions of 5% hydrochloric acid, once with 20 ml. of sodium bicarbonate and finally with 15 ml. of brine. Drying over anhydrous magnesium sulphate and removal of the solvent in vacuo gave the desired 3-(6-cyanohexyl)-2-methoxymethyl levulinaldehyde (0.195 g., 78% yield). Infra-red and proton NMR spectroscopy were in agreement with the proposed structure.

Workup

  1. additionTo a mixture of 1.874 g
  2. stirringThe reaction mixture was stirred at room temperature for 0.5 hr
  3. custom, at the end of which the supernatant was decanted into a separatory funnel
  4. washThe residue was washed several times with diethyl ether (total 150 ml.)
  5. washThe combined organic solutions were washed three times with 20 ml
  6. dry with materialDrying over anhydrous magnesium sulphate and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-0a5160ee23aa4dd9bbff9f0f9f002fd2
Source dataset
uspto-grants-1976_08
Patent number
US03976678

Reaction notes

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