Pyridine → HCID 13506639, compound

HRID 1488881Notes

Reaction equation

HRID 1488881 reaction equation
[CH2:1]([OH:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].N1C=CC=CC=1.Cl[C:19]([O:21][CH:22]([Cl:24])[CH3:23])=[O:20]>ClCCl>[C:19](=[O:20])([O:11][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[O:21][CH:22]([Cl:24])[CH3:23]

Participants

5

Reactant 3

HCID 1049PyridineHCID 81741-DecanolHCID 5213051-Chloroethyl chloroformate

Product 1

HCID 13506639HCID 13506639, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of decanol (6.0 g, 7.23 mmol) in dichloromethane (150 ml) was added dry pyridine (3.66 ml, 45.6 mmol). The solution was cooled in an ice bath. To this was added 1-chloroethyl chloroformate (6.5 g, 45.6 mmol) dropwise. The reaction mixture was allowed to proceed overnight, diluted with dichloromethane and washed with 0.5N HCl solution, twice with a saturated sodium bicarbonate solution and finally with distilled water. The solvent was dried over magnesium sulphate, filtered through silica and concentrated to dryness. Yield: 93%.

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. washwashed with 0.5N HCl solution, twice with a saturated sodium bicarbonate solution and finally with distilled water
  3. dry with materialThe solvent was dried over magnesium sulphate
  4. filtrationfiltered through silica
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-149c264b651c4941a6d701fd3ad5ef0e
Source dataset
uspto-grants-1997_10
Patent number
US05676925

Reaction notes

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