Hydrochloric Acid → HCID 13457163, compound

HRID 2232380Notes

Reaction equation

HRID 2232380 reaction equation
[H-].[Na+].[CH3:3][C:4]1[N:5]([CH2:11][CH2:12][OH:13])[C:6]([CH3:10])=[C:7]([CH3:9])[N:8]=1.Cl[CH2:15][C:16](=[O:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].Cl>O1CCCC1>[CH3:3][C:4]1[N:5]([CH2:11][CH2:12][O:13][CH2:15][C:16](=[O:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:6]([CH3:10])=[C:7]([CH3:9])[N:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 69484Ethyl 4-chloroacetoacetateHCID 212836882-(2,4,5-Trimethyl-1H-imidazol-1-yl)ethan-1-ol

Product 1

HCID 13457163HCID 13457163, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (80% dispersion in oil) (7.8 g) was suspended in dry tetrahydrofuran (100 ml). 2-(2,4,5-Trimethylimidazol-1-yl)ethanol (20 g) was added and the suspension sonicated until there was no further gas evolution. Ethyl 4-chloroacetoacetate (21.3 g) in dry tetrahydrofuran (25 ml) was added over 0.75 hours with sonication, and sonication continued for a further 4 hours. The suspension was poured into 2N hydrochloric acid (200 ml) and the tetrahydrofuran removed under vacuum. The aqueous solution was washed with dichloromethane (3×50 ml) and then neutralised with potassium carbonate. The aqueous phase was extracted with dichloromethane (5×100 ml), the combined organic extracts dried over magnesium sulphate and solvent removed under vacuum. The crude product was chromatographed over silica eluting with a mixture of methanol and ethyl acetate (1:3) to yield the title compound as a pale red oil 13.5 g (37%).

Workup

  1. customthe suspension sonicated until there
  2. customthe tetrahydrofuran removed under vacuum
  3. washThe aqueous solution was washed with dichloromethane (3×50 ml)
  4. extractionThe aqueous phase was extracted with dichloromethane (5×100 ml)
  5. dry with materialthe combined organic extracts dried over magnesium sulphate and solvent
  6. customremoved under vacuum
  7. customThe crude product was chromatographed over silica eluting with a mixture of methanol and ethyl acetate (1:3)

Sources & evidence

ORD record
ord-2a764efc0d494d2d90fe3ffad7733ede
Source dataset
uspto-grants-1988_11
Patent number
US04788205

Reaction notes

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