Water → 4-acetyloxy-3,5-dimethyl-6-(5-formylbenzofuran-2-yl)-2H-pyran-2-one

HRID 1357199Notes

Reaction equation

HRID 1357199 reaction equation
CCN(CC)CC.[CH3:8][C:9]1[C:10](=[O:28])[O:11][C:12]([C:17]2[O:18][C:19]3[CH:25]=[CH:24][C:23]([CH:26]=[O:27])=[CH:22][C:20]=3[CH:21]=2)=[C:13]([CH3:16])[C:14]=1[OH:15].[C:29](Cl)(=[O:31])[CH3:30].O>C(Cl)Cl.CCOC(C)=O>[C:29]([O:15][C:14]1[C:13]([CH3:16])=[C:12]([C:17]2[O:18][C:19]3[CH:25]=[CH:24][C:23]([CH:26]=[O:27])=[CH:22][C:20]=3[CH:21]=2)[O:11][C:10](=[O:28])[C:9]=1[CH3:8])(=[O:31])[CH3:30]

Participants

7

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 547277123,5-dimethyl-6-(5-formylbenzofuran-2-yl)-4-hydroxy-2H-pyran-2-one

Product 1

HCID 154628324-acetyloxy-3,5-dimethyl-6-(5-formylbenzofuran-2-yl)-2H-pyran-2-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

After adding Et3N (1.7 g) to a suspension of 3,5-dimethyl-6-(5-formylbenzofuran-2-yl)-4-hydroxy-2H-pyran-2-one (5.0 g) in CH2Cl2 (100 ml), the mixture was cooled on ice, acetyl chloride (1.32 g) was added and the mixture was stirred at room temperature for one hour. Water (100 ml) was added to the reaction solution, 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=3/1) to obtain 4-acetyloxy-3,5-dimethyl-6-(5-formylbenzofuran-2-yl)-2H-pyran-2-one.

Workup

  1. additionwas added
  2. dry with materialthe organic layer was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=3/1)

Sources & evidence

ORD record
ord-c4fbe88377da412ba1b6862705cbc702
Source dataset
uspto-grants-2003_07
Patent number
US06589984B1

Reaction notes

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