Hydrochloric Acid → 3,5-dimethyl-4-hydroxy-6-(5-methoxybenzofuran-2-yl)-2H-pyran-2-one

HRID 1357203Notes

Reaction equation

HRID 1357203 reaction equation
[C:1]([O-:4])([O-])=O.[K+].[K+].Br[CH2:8][C:9]1[O:14][C:13](=[O:15])[C:12]([CH3:16])=[C:11]([O:17]COC)[C:10]=1[CH3:21].Cl.CN([CH:26]=[O:27])C>>[CH3:16][C:12]1[C:13](=[O:15])[O:14][C:9]([C:8]2[O:27][C:26]3[CH:13]=[CH:12][C:11]([O:4][CH3:1])=[CH:10][C:9]=3[CH:8]=2)=[C:10]([CH3:21])[C:11]=1[OH:17]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 120829716-bromomethyl-3,5-dimethyl-4-methoxymethoxy-2H-pyran-2-one

Product 1

HCID 546827763,5-dimethyl-4-hydroxy-6-(5-methoxybenzofuran-2-yl)-2H-pyran-2-one

Procedure

K2CO3 (138 mg) was added to a solution of 5-methoxysalicyl aldehyde (152 mg) and 6-bromomethyl-3,5-dimethyl-4-methoxymethoxy-2H-pyran-2-one (277 mg) in DMF (5 ml), and the mixture was stirred at room temperature for 16 hours. A 6 N hydrochloric acid aqueous solution was slowly added to the reaction solution, and after stirring for one hour, extraction was performed with AcOEt and the organic layer was dried with MgSO4 and then filtered and concentrated. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=1/1) to obtain 3,5-dimethyl-4-hydroxy-6-(5-methoxybenzofuran-2-yl)-2H-pyran-2-one.

Workup

  1. stirringafter stirring for one hour
  2. extractionextraction
  3. dry with materialthe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=1/1)

Sources & evidence

ORD record
ord-a52dbc39a06b450abf63a3507d025fb7
Source dataset
uspto-grants-2003_07
Patent number
US06589984B1

Reaction notes

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