Pyridine → 1-Chloroethyl 1-methylethyl carbonate

HRID 537331Notes

Reaction equation

HRID 537331 reaction equation
[CH3:1][CH:2]([OH:4])[CH3:3].N1C=CC=CC=1.Cl[C:12]([O:14][CH:15]([Cl:17])[CH3:16])=[O:13]>>[C:12](=[O:13])([O:4][CH:2]([CH3:3])[CH3:1])[O:14][CH:15]([Cl:17])[CH3:16]

Participants

4

Reactant 3

HCID 1049PyridineHCID 3776IsopropanolHCID 5213051-Chloroethyl chloroformate

Product 1

HCID 117895851-Chloroethyl 1-methylethyl carbonateYield 88%

Conditions

Temperature
25 °C

Procedure

To a solution of 2-propanol (2.66 mL, 34.97 mmol) and pyridine (3.39 mL, 41.96 mmol), pre-cooled in a dry-ice/acetone bath was slowly added 1-chloroethyl chloroformate. The resulting mixture was allowed to slowly warm to 25° C. overnight, with stirring. After concentration under reduced pressure the mixture was dissolved in ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give 1-chloroethyl isopropyl carbonate as a pink/orange oil (5.11 g, 88% yield).

Workup

  1. concentrationAfter concentration under reduced pressure the mixture
  2. dissolutionwas dissolved in ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ecdaf4ea10644ec69480505403fda354
Source dataset
uspto-grants-2014_10
Patent number
US08859781B2

Reaction notes

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