Pyridine → 6,6-Dimethylbicyclo[3.1.1]hept-2-ene 2-ethyl chloroformate

HRID 328344Notes

Reaction equation

HRID 328344 reaction equation
[CH3:1][C:2]1([CH3:12])[CH:7]2[CH2:8][CH:3]1[CH2:4][CH:5]=[C:6]2[CH2:9][CH2:10][OH:11].N1C=CC=CC=1.[C:19](Cl)([Cl:21])=[O:20].Cl.N1C=CC=CC=1>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:12])[CH:3]2[CH2:8][CH:7]1[CH2:6][CH:5]=[CH:4]2.[Cl:21][C:19]([O:11][CH2:10][CH3:9])=[O:20]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6371PhosgeneHCID 31408NopolHCID 10176127Pyridinium chloride

Product 1

HCID 888259916,6-Dimethylbicyclo[3.1.1]hept-2-ene 2-ethyl chloroformate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

16.6 G. (0.1 mole) of 6,6-dimethylbicyclo-[3.1.1]hept-2-ene-2-ethanol and 7.9 g. (8.1 ml., 0.1 mole) of pyridine are thoroughly mixed and added dropwise at 10° C to 125 ml. (0.2 moles) of 17.2% phosgene and benzene over a period of 20 minutes. A white precipitate of pyridine hydrochloride forms immediately. The reaction mixture is stirred in the cold for one hour and at room temperature overnight. A stream of nitrogen is passed through the mixture to remove the excess phosgene and the solution is filtered. The filtrate is evaporated to dryness in vacuo affording 23.4 g. (quantitative yield) of 6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-ethyl chloroformate which infrared analysis indicates to be pure material.

Workup

  1. additionadded dropwise at 10° C to 125 ml
  2. customat room temperature
  3. customovernight
  4. customto remove the excess phosgene
  5. filtrationthe solution is filtered
  6. customThe filtrate is evaporated to dryness in vacuo
  7. customaffording 23.4 g

Sources & evidence

ORD record
ord-3d45309808394174ad53405045291e88
Source dataset
uspto-grants-1977_04
Patent number
US04017505

Reaction notes

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