Pyridine → Chloromethyl pentan-3-yl carbonate

HRID 1290883Notes

Reaction equation

HRID 1290883 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].S(Cl)([Cl:9])(=O)=O.[CH3:11][CH2:12][CH:13]([OH:16])[CH2:14][CH3:15].N1C=CC=CC=1>CCCCCC.N(C(C)(C)C#N)=NC(C)(C)C#N>[CH3:11][CH2:12][CH:13]([O:16][C:2]([O:4][CH2:5][Cl:9])=[O:3])[CH2:14][CH3:15]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 114283-PentanolHCID 24648Sulfuryl chloride

Product 1

HCID 54403423Chloromethyl pentan-3-yl carbonateYield 55%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 8058HexaneSolvent2×

Procedure

A mixture of methyl chloroformate (25.0 g), sulfuryl chloride (35.7 g) and α,α'-azobis(isobutyronitrile) (100 mg) is refluxed for 8 hours. After cooling, the reaction mixture is diluted with hexane (150 ml) and 3-pentanol (24.0 g) is added thereto. Pyridine (42.0 g) is added dropwise to the mixture for 20 minutes under ice-cooling and stirring. After the mixture is stirred at room temperature overnight, hexane (200 ml) is added thereto. The reaction mixture is washed with water, dried, filtered and evaporated to remove the solvent. The residue is distilled under reduced pressure to give 3-pentyloxycarbonyloxymethyl chloride (26.3 g).

Workup

  1. temperatureis refluxed for 8 hours
  2. temperatureAfter cooling
  3. additionis added
  4. temperaturecooling
  5. stirringAfter the mixture is stirred at room temperature overnight
  6. washThe reaction mixture is washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customto remove the solvent
  11. distillationThe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-9c66815f47064c2daad77b78cf0d3c08
Source dataset
uspto-grants-1998_05
Patent number
US05753672

Reaction notes

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