Imidazole → HCID 54686174, compound

HRID 1757044Notes

Reaction equation

HRID 1757044 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[O:5][C:4](=[O:10])[CH:3]=1.N1C=CN=C1.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].O>CN(C)C=O>[Si:16]([O:9][CH2:8][C:6]1[O:5][C:4](=[O:10])[CH:3]=[C:2]([OH:1])[CH:7]=1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 546861756328-86-5

Product 1

HCID 54686174HCID 54686174, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Hydroxy-6-hydroxymethylpyran-2-one (14.6 parts) was dissolved in dimethyl formamide (30 parts) at 20° C., imidazole (17.2 parts) was added and the temperature of the mixture cooled to 13° C. t-Butyldimethylsilyl chloride (17.1 parts) was then added in portions, the temperature was allowed to rise to 25° C. and maintained at 25°-30° C. by external cooling. The mixture was stirred for a further hour at 25°-30° C., before pouring into water (1100 parts) and stirring for 30 minutes until the product crystallised. The product was filtered off, washed with water (2×200 parts) and dried at 40° C./20 mm to give 6-t-butyldimethylsilyloxymethyl-4-hydroxy pyran-2-one (12.1 parts, 47%) m.pt 139°-141° C. Extraction of the filtrates with dichlorometane gave a further 7.0 parts, 27% of the product.

Workup

  1. additionwas then added in portions
  2. customto rise to 25° C.
  3. temperaturemaintained at 25°-30° C. by external cooling
  4. stirringstirring for 30 minutes until the product
  5. customcrystallised
  6. filtrationThe product was filtered off
  7. washwashed with water (2×200 parts)
  8. customdried at 40° C./20 mm

Sources & evidence

ORD record
ord-70e6b77fe1994fb19e5ffc98ada57e62
Source dataset
uspto-grants-1995_08
Patent number
US05443970

Reaction notes

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