Chloroform → HCID 59299840, compound

HRID 385589Notes

Reaction equation

HRID 385589 reaction equation
[CH3:1][C:2]1[C:3](=[O:16])[CH:4]=[C:5]([CH2:8][O:9]C2CCCCO2)[O:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].C(Cl)(Cl)Cl>CO.Cl>[OH:9][CH2:8][C:5]1[O:6][CH:7]=[C:2]([CH3:1])[C:3](=[O:16])[CH:4]=1

Participants

6

Reactant 3

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 57815481HCID 57815481, compound

Product 1

HCID 59299840HCID 59299840, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 0.61 g of 5-methyl-2-((tetrahydro-2H-pyran-2-yloxy)methyl)-4H-pyran-4-one in 3 mL of methanol, 0.03 mL of concentrated hydrochloric acid was added, and the mixture was stirred at room temperature for 1 hour. To the reaction mixture, 0.5 g of potassium carbonate and chloroform were added, and the mixture was stirred for 30 minutes. The insoluble substance was filtered off, the solvent was distilled off under reduced pressure, and the resultant residue was purified by silica gel column chromatography using an eluent of chloroform:methanol=9:1 to obtain 0.26 g of 2-hydroxymethyl-5-methyl-4H-pyran-4-one as a white solid.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. filtrationThe insoluble substance was filtered off
  3. distillationthe solvent was distilled off under reduced pressure
  4. customthe resultant residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-201068cf35b64109ab5f2553e0415ffa
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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