Pyridine → HCID 22463561, compound

HRID 1937253Notes

Reaction equation

HRID 1937253 reaction equation
[C:1]12([OH:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][C:3]([OH:11])([CH2:4]3)[CH2:2]1)[CH2:8]2.N1C=CC=CC=1.[CH3:19][O:20][C:21](Cl)=[O:22]>CN(C=O)C>[CH3:19][O:20][C:21]([O:12][C:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][C:3]([O:11][C:21]([O:20][CH3:19])=[O:22])([CH2:4]3)[CH2:2]1)[CH2:8]2)=[O:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 5738291,3-Adamantanediol2×

Product 1

HCID 22463561HCID 22463561, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In an atmosphere of nitrogen, 10 mmole of 1,3-adamantanediol and 24 mmole of pyridine were dissolved in 10 mL of DMF. To the mixture, 22 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-adamantanediol was 99% and 1,3-bis (methoxycarbonyloxy)adamantane (yield 90%) 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-1bb26664d2ba41b0907e20ccf76ad2c7
Source dataset
uspto-grants-2002_05
Patent number
US06392104B1

Reaction notes

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