1,1'-Carbonyldiimidazole → HCID 69662350, compound

HRID 411551Notes

Reaction equation

HRID 411551 reaction equation
[C:1]([O:4][CH2:5][C:6]([OH:9])([CH3:8])[CH3:7])(=[O:3])[CH3:2].[C:10](N1C=CN=C1)([N:12]1[CH:16]=[CH:15][N:14]=[CH:13]1)=[O:11]>C(Cl)Cl>[N:12]1([C:10]([O:9][C:6]([CH3:8])([CH3:7])[CH2:5][O:4][C:1](=[O:3])[CH3:2])=[O:11])[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 110839221,2-Propanediol, 2-methyl-, 1-acetate

Product 1

HCID 69662350HCID 69662350, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-hydroxy-2-methylpropyl acetate (3.35 g, 25.3 mmol) and 1,1′-carbonyldiimidazole (4.11 g, 25.3 mmol) in DCM was stirred for 8 h at rt. The mixture was then transferred to a closed vessel and heated to 100° C. overnight. The mixture was concentrated in vacuo before ether and water were added. The organic phase was separated, dried and concentrated in vacuo. The resulting residue was purified by chromatography on silica gel, eluting with THF:heptane (1:1), to give the title compound in 20% yield.

Workup

  1. customThe mixture was then transferred to a closed vessel
  2. temperatureheated to 100° C. overnight
  3. concentrationThe mixture was concentrated in vacuo before ether and water
  4. additionwere added
  5. customThe organic phase was separated
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified by chromatography on silica gel
  9. washeluting with THF:heptane (1:1)

Sources & evidence

ORD record
ord-1ce519a6f46d472ab6a37ab909b785f8
Source dataset
uspto-grants-2003_05
Patent number
US06559162B2

Reaction notes

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