Pyridine → Chloromethyl 1,1-dimethylethyl carbonate

HRID 1033611Notes

Reaction equation

HRID 1033611 reaction equation
N1C=CC=CC=1.Cl[C:8]([O:10][CH2:11][Cl:12])=[O:9].[CH3:13][C:14]([OH:17])([CH3:16])[CH3:15]>C(Cl)Cl>[C:8](=[O:9])([O:10][CH2:11][Cl:12])[O:17][C:14]([CH3:16])([CH3:15])[CH3:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6386tert-ButanolHCID 62754Chloromethyl chloroformate

Product 1

HCID 13557092Chloromethyl 1,1-dimethylethyl carbonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

0.62 mL pyridine was added dropwise to a solution of 0.77 g chloromethyl chloroformate and 1.32 mL t-BuOH in 60 mL CH2Cl2 cooled in an ice bath under an Ar atmosphere. The reaction was stirred 2 hours at 0° C. then transferred to a separatory funnel. The reaction was washed twice with H2O, once with 10% CuSO4, once with brine and dried with MgSO4. Suction filtration and evaporation provided 0.55 g of desired product which was used without purification.

Workup

  1. temperaturecooled in an ice bath under an Ar atmosphere
  2. customthen transferred to a separatory funnel
  3. washThe reaction was washed twice with H2O, once with 10% CuSO4, once with brine
  4. dry with materialdried with MgSO4
  5. filtrationSuction filtration and evaporation

Sources & evidence

ORD record
ord-5dccc3a2c61b4b3fa011be8e8da9bb6d
Source dataset
uspto-grants-1994_05
Patent number
US05310929

Reaction notes

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