Methyl chloroformate → HCID 12070476, compound

HRID 1937259Notes

Reaction equation

HRID 1937259 reaction equation
[CH3:1][O:2][C:3](Cl)=[O:4].[C:6]12([OH:18])[CH2:15][C:10]3([OH:16])[CH2:11][CH:12]([CH2:14][C:8]([OH:17])([CH2:9]3)[CH2:7]1)[CH2:13]2>CN(C=O)C>[CH3:1][O:2][C:3]([O:18][C:6]12[CH2:15][C:10]3([O:16][C:3]([O:2][CH3:1])=[O:4])[CH2:11][CH:12]([CH2:14][C:8]([O:17][C:3]([O:2][CH3:1])=[O:4])([CH2:9]3)[CH2:7]1)[CH2:13]2)=[O:4]

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 98990221,3,5-Adamantanetriol

Product 1

HCID 12070476HCID 12070476, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In an atmosphere of nitrogen, 10 mmole of 1,3,5-adamantanetriol obtained by the method of Example 32 and 36 mmole of pyridine were dissolved in 10 mL of DMF. To the mixture, 33 mmole of methoxycarbonyl chloride was added dropwise with stirring at room temperature. Cooling of the resultant mixture with ice was started at about the time exothermic reaction began. When the exothermic reaction is completed, the mixture was heated to 60° C. and then stirred for one hour. As a result, the conversion of 1,3,5-adamantanetriol was 99% and 1,3,5-tris(methoxycarbonyloxy)adamantane (yield 95%) was formed.

Workup

  1. customwas started at about the time exothermic reaction
  2. customWhen the exothermic reaction
  3. temperaturethe mixture was heated to 60° C.
  4. stirringstirred for one hour

Sources & evidence

ORD record
ord-19674e3f3dad49c3936a79eaadf45501
Source dataset
uspto-grants-2002_05
Patent number
US06392104B1

Reaction notes

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