1,1'-Carbonyldiimidazole → HCID 69662350, compound

HRID 857188Notes

Reaction equation

HRID 857188 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-d1c66f5f4c4545aa97dfd233f1fa1167
Source dataset
uspto-grants-2006_12
Patent number
US07144914B2

Reaction notes

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