Bicarbonate Ion → HCID 58083656, compound

HRID 2283223Notes

Reaction equation

HRID 2283223 reaction equation
N1C=CN=C1.[OH:6][C:7]1[C:12](=[O:13])[CH:11]=[CH:10][O:9][C:8]=1[CH3:14].[C:15]([Si:19]([CH3:22])([CH3:21])Cl)([CH3:18])([CH3:17])[CH3:16].C(=O)([O-])O>CN(C)C=O>[Si:19]([O:6][C:7]1[C:12](=[O:13])[CH:11]=[CH:10][O:9][C:8]=1[CH3:14])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 769Bicarbonate IonHCID 795ImidazoleHCID 8369MaltolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 58083656HCID 58083656, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of imidazole (Im, 5.45 g, 0.08 mol) in N,N-dimethylformamide (20 ml) is added in an inert atmosphere and dropwise to a solution containing 3-hydroxy-2-methyl-4-pyrone (5.00 g, 0.04 mol) and tert-butyl-dimethylchlorosilane (TBDMSCl, 7.00 g, 0.044 mol) in N,N-dimethylformamide (100 ml). The mixture obtained thereby is maintained stirring at a room temperature for 6 h and then diluted by adding a 5% hydrogen carbonate aqueous solution (150 ml). The mixture obtained thereby is extracted with hexane (6×50 ml); the extracted organic phases are combined, anhydrified on sodium sulphate, and evaporated under vacuum obtaining the desired 3-(tert-butyl-dimethylsilyl)oxy-2-methyl-4-pyrone compound as a colourless crystalline solid (9.61 g).

Workup

  1. customThe mixture obtained
  2. temperaturethereby is maintained
  3. additiondiluted
  4. customThe mixture obtained
  5. extractionthereby is extracted with hexane (6×50 ml)
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-0a5b28f4f27e44f3b081764af26c1bf9
Source dataset
uspto-grants-2015_09
Patent number
US09145381B2

Reaction notes

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