Acetic Anhydride → HCID 18519037, compound

HRID 1369283Notes

Reaction equation

HRID 1369283 reaction equation
[CH:1]([C:3]1[C:4]2[C:14]([CH:15]=[CH:16][CH:17]=1)=[CH:13][C:7]1[C:8](=[O:12])[O:9][CH:10]([OH:11])[C:6]=1[CH:5]=2)=[O:2].[CH3:18][C:19](OC(C)=O)=[O:20]>[Cl-].[Na+].O>[C:19]([O:11][CH:10]1[O:9][C:8](=[O:12])[C:7]2[CH:13]=[C:14]3[C:4](=[CH:5][C:6]1=2)[C:3]([CH:1]=[O:2])=[CH:17][CH:16]=[CH:15]3)(=[O:20])[CH3:18]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 18519029HCID 18519029, compound

Product 1

HCID 18519037HCID 18519037, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 5-formyl-3-hydroxynaphtho[2,3-c]furan-1(3H)-one (190 mg, 0.83 mmol) pyridine (1.66 mL) at rt was added Ac2O (126 mg, 0.117 mL, 1.25 mmol). The solution was stirred at rt for 18 hours and then poured into brine and extracted with EtOAc. The extract was dried over MgSO4 and concentrated The crude material was chromatographed on silica get (3:1 hexanes:EtOAc) to give the title compound (100 mg, 44%).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe extract was dried over MgSO4
  3. concentrationconcentrated The crude material
  4. customwas chromatographed on silica
  5. customget (3:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-8c8cc71f403146bf9cbae9f984d3bd1b
Source dataset
uspto-grants-2003_06
Patent number
US06576766B1

Reaction notes

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