Tetrahydrofuran → HCID 22325281, compound

HRID 496347Notes

Reaction equation

HRID 496347 reaction equation
[OH-:1].[Na+].C([O:6][CH:7]([C:16]1C(C)=C(OC)[C:19]([O:25][CH3:26])=[C:18]([O:27][CH3:28])[C:17]=1[O:29][CH3:30])[C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1)(=O)C.[CH2:31]1[CH2:35][O:34][CH2:33][CH2:32]1>[N+]([O-])([O-])=O.[Ag+]>[OH:6][CH:7]([C:16]1[C:31]([CH3:32])=[C:35]([O:34][CH3:33])[C:19]([O:25][CH3:26])=[C:18]([O:27][CH3:28])[C:17]=1[O:29][CH3:30])[C:8]1[CH:9]=[CH:10][C:11]([C:12]([OH:13])=[O:1])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22325308HCID 22325308, compound

Product 1

HCID 22325281HCID 22325281, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 24470Silver NitrateCatalyst

Procedure

After adding dropwise an aqueous solution (20 ml) of silver nitrate (3.06 g, 18.00 mmol) to an aqueous solution of 1 N sodium hydroxide (36 ml), a solution of 4-[acetoxy-(2,3,4,5-tetramethoxy-6-methylphenyl)methyl]benzaldehyde (2.34 g, 6.00 mmol) obtained in Step 2 of Example 1 in THF (30 ml) was added dropwise and the mixture was stirred at room temperature for 5 hours. The reaction mixture was filtered and the solid was washed with hot water. The filtrate and the wash solution were combined, which was then acidified with concentrated hydrochloric acid and then was extracted with ether. The extract was dried and the solvent was distilled off to yield the title compound (2.3 g, 6.37 mmol, yield 100%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solid was washed with hot water
  3. extractionwas extracted with ether
  4. customThe extract was dried
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-322fb19bcf544401b1936520ebc1f2da
Source dataset
uspto-grants-2005_09
Patent number
US06943196B1

Reaction notes

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