Pyridine → HCID 13645651, compound

HRID 2352128Notes

Reaction equation

HRID 2352128 reaction equation
N1C=CC=CC=1.[CH3:7][CH:8]([CH3:17])[CH:9]([C:11]1[CH:12]=[N:13][CH:14]=[N:15][CH:16]=1)[OH:10].CCOCC>ClCCl.[O-2].[Cr+6].[O-2].[O-2]>[CH3:7][CH:8]([CH3:17])[C:9]([C:11]1[CH:16]=[N:15][CH:14]=[N:13][CH:12]=1)=[O:10]

Participants

6

Reactant 3

HCID 1049PyridineHCID 3283Diethyl EtherHCID 11744819HCID 11744819, compound

Product 1

HCID 13645651HCID 13645651, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of chromium (VI) oxide (12.87 g, 65 mmol) in dry dichloromethane (500 ml) was added dry pyridine (10.27 g, 130 mmol) and the mixture stirred for 0.5 h. Then a solution of 2-methyl-1-(pyrimid-5-yl)-propan-1-ol, prepared in stage 1, (1.52 g, 10 mmol) in dry dichloromethane (100 ml) was added dropwise with stirring. After 2 hours the reaction mixture was poured into ether (1000 ml) and then filtered. The filtrate was washed with copper sulphate solution (4×400 ml), brine solution (2×400 ml), and dried over magnesium sulphate before removing the solvent. Flash chromatography (silica gel, petrol/ether elution) gave the product as a colourless oil (0.72 g, 48%).

Workup

  1. additionwas added dropwise
  2. stirringwith stirring
  3. filtrationfiltered
  4. washThe filtrate was washed with copper sulphate solution (4×400 ml), brine solution (2×400 ml)
  5. dry with materialdried over magnesium sulphate
  6. custombefore removing the solvent
  7. washFlash chromatography (silica gel, petrol/ether elution)

Sources & evidence

ORD record
ord-9a32f9acf9cd48d9bfb6c0a17a70c26b
Source dataset
uspto-grants-1989_10
Patent number
US04875922

Reaction notes

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