Methyl chloroformate → HCID 18783161, compound

HRID 1420874Notes

Reaction equation

HRID 1420874 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].Cl.[CH3:7][NH:8][C:9]1([CH3:19])[CH2:14][C:13]([CH3:16])([CH3:15])[CH2:12][C:11]([CH3:18])([CH3:17])[CH2:10]1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.O>[CH3:5][O:4][C:2]([N:8]([CH3:7])[C:9]1([CH3:19])[CH2:14][C:13]([CH3:15])([CH3:16])[CH2:12][C:11]([CH3:18])([CH3:17])[CH2:10]1)=[O:3]

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 10340Sodium CarbonateHCID 18783153HCID 18783153, compound

Product 1

HCID 18783161HCID 18783161, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl chloroformate (0.97 g, 0.8 ml, 10.3 mmol) was added in one portion to a suspension of N,1,3,3,5,5-hexamethylcyclohexanamine hydrochloride (5-20) (1.13 g, 5.13 mmol) and Na2CO3 (1.63 g, 15.4 mmol) in THF (30 ml). The resulting mixture was stirred at room temperature for 6 h, and then it was diluted with water (50 ml) and extracted with ether (3*30ml). The combined organic phases were washed with 10% K2SO4, saline, dried over MgSO4, filtered and evaporated. The crude product was purified by flash chromatography, eluting with hexane-ethyl acetate mixture (6:1) to give 0.90 g (78%) of (15) as an oil.

Workup

  1. extractionextracted with ether (3*30ml)
  2. washThe combined organic phases were washed with 10% K2SO4, saline
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by flash chromatography
  7. washeluting with hexane-ethyl acetate mixture (6:1)

Sources & evidence

ORD record
ord-dcb12e24cdeb48da836c50352b8b994d
Source dataset
uspto-grants-2000_06
Patent number
US06071966

Reaction notes

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