Imidazole → HCID 21255857, compound

HRID 481710Notes

Reaction equation

HRID 481710 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH:2]([CH2:4][OH:5])[OH:3].N1C=CN=C1.[Si:14](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCCC1>[Si:14]([O:5][CH2:4][CH:2]([OH:3])[C:1]([O:7][CH3:8])=[O:6])([C:27]([CH3:30])([CH3:29])[CH3:28])([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 140003Methyl 2,3-dihydroxypropanoate

Product 1

HCID 21255857HCID 21255857, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl glycerate (25.88 g, 215 mmol) and imidazole (22.0 g, 323 mmol, 1.5 eq) in tetrahydrofuran (250 mL) was added t-butyldiphenylsilyl chloride (53.0 mL, 204 mmol, 0.95 eq) at 0° C. After stirring for 18 h the reaction was quenched by the addition of saturated ammonium chloride and the aqueous phase was extracted with dichloromethane. The organic layer was dried with magnesium sulfate and evaporated under reduced pressure. The crude material was purified by flash chromatography with a mixture of hexanes and ethyl acetate (80:20) to give the compound (68.89 g) in 94% yield. 1H NMR (300 MHz, CDCl3) δ: 1.04 (s, 9H, t-butyl), 3.80 (s, 3H, CO2 CH3), 3.93 (dd, 1H, J=2.9 Hz, 9.0 Hz, H-3a), 3.98 (dd, 1H, J=2.9 Hz, 9.0 Hz, H-3b), 4.26 (dd, 1H, J=2.9 Hz, 2.9 Hz, H-2), 7.42 and 7.65 (m, 10H, Ar-H).

Workup

  1. customwas quenched by the addition of saturated ammonium chloride
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe crude material was purified by flash chromatography with a mixture of hexanes and ethyl acetate (80:20)

Sources & evidence

ORD record
ord-c2c72a05c8b34b2aa7632383e347e3dd
Source dataset
uspto-grants-1998_08
Patent number
US05789394

Reaction notes

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