Pyridine → 1-Methylcyclobutyl Chloroformate

HRID 1605182Notes

Reaction equation

HRID 1605182 reaction equation
[CH3:1][C:2]1([OH:6])[CH2:5][CH2:4][CH2:3]1.N1C=CC=CC=1.[C:13](Cl)([Cl:15])=[O:14]>C1C=CC=CC=1>[Cl:15][C:13]([O:6][C:2]1([CH3:1])[CH2:5][CH2:4][CH2:3]1)=[O:14]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6371PhosgeneHCID 1406421-Methylcyclobutanol

Product 1

HCID 215491141-Methylcyclobutyl Chloroformate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 0.55 gm. (6.5 mM) of 1-methylcyclobutanol, and 0.44 ml. of pyridine in 10 ml. of benzene is added to a solution of phosgene in 10 ml. of benzene at 0°C. over a 30 minute period. The reaction is allowed to stir for 30 minutes and then filtered to remove pyridine hydrochloride formed during the reaction. Excess phosgene is removed by evaporation at reduced pressure and the volume of the benzene solution is reduced to 4-5 ml; the benzene solution of 1-methylcyclobutylchloroformate is employed in the following reaction.

Workup

  1. filtrationfiltered
  2. customto remove pyridine hydrochloride
  3. customformed during the reaction
  4. customExcess phosgene is removed by evaporation at reduced pressure
  5. customthe benzene solution of 1-methylcyclobutylchloroformate is employed in the following reaction

Sources & evidence

ORD record
ord-8e138047a8a8435da83816e687439254
Source dataset
uspto-grants-1976_04
Patent number
US03948971

Reaction notes

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