Pyridine → 2-Methyl-2-nitro-1,3-propanediol ditriflate

HRID 2060938Notes

Reaction equation

HRID 2060938 reaction equation
S([O:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])(C(F)(F)F)(=O)=O.[CH3:16][C:17]([N+:22]([O-:24])=[O:23])([CH2:20]O)[CH2:18][OH:19].N1C=CC=CC=1>C(Cl)(Cl)Cl>[S:9]([O:19][CH2:18][C:17]([CH3:20])([N+:22]([O-:24])=[O:23])[CH2:16][O:8][S:9]([C:12]([F:13])([F:14])[F:15])(=[O:10])=[O:11])([C:12]([F:15])([F:14])[F:13])(=[O:10])=[O:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 64802-Methyl-2-nitro-1,3-propanediolHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 593936202-Methyl-2-nitro-1,3-propanediol ditriflate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of triflic anhydride (16.5 ml, 0.1 mol) in chloroform (50 ml) is added a solution of 2-methyl-2-nitro-1,3-propanediol (6.75 g, 0.05 mol) and pyridine (8.85 ml, 0.11 mol) in chloroform (50 ml) with external cooling to ensure a temperature of between 0° and 5° C. during the addition. After the addition the cooling bath is removed and the reaction stirred for 18 hours at ambient temperature. The reaction mixture is transferred to a separating funnel and washed with water. The organic layer is dried (Na2SO4), filtered and evaporated to dryness. The crude product is purified by chromatography using a 4:1 mixture of Hexane:Ethyl acetate as eluant; the product is obtained as a solid with melting point 50-52° C.

Workup

  1. temperaturewith external cooling
  2. customa temperature of between 0° and 5° C.
  3. additionduring the addition
  4. additionAfter the addition the cooling bath
  5. customis removed
  6. customThe reaction mixture is transferred to a separating funnel
  7. washwashed with water
  8. dry with materialThe organic layer is dried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated to dryness
  11. customThe crude product is purified by chromatography
  12. additiona 4:1 mixture of Hexane
  13. customthe product is obtained as a solid with melting point 50-52° C.

Sources & evidence

ORD record
ord-f19362a3d07943a2a7aae1dc38c6bf32
Source dataset
uspto-grants-2012_10
Patent number
US08278464B2

Reaction notes

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