Acetic Acid → HCID 18519064, compound

HRID 1369286Notes

Reaction equation

HRID 1369286 reaction equation
O[CH:2]1[C:6]2[C:7]3[C:12]([CH:13]=[CH:14][C:5]=2[C:4](=[O:18])[O:3]1)=[C:11]([C:15]([OH:17])=[O:16])[CH:10]=[CH:9][CH:8]=3.CC1C=CC(S(O)(=O)=O)=CC=1.[CH:30](OC)([O:33]C)[O:31][CH3:32].CC(O)=O>CO.C([O-])(O)=O.[Na+]>[OH:17][C:15]([C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[CH:13]=[CH:14][C:5]1[C:4](=[O:18])[O:3][CH:2]([C:30]([O:31][CH3:32])=[O:33])[C:6]=12)=[O:16]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 18519034HCID 18519034, compound

Product 1

HCID 18519064HCID 18519064, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 1-hydroxy-6-hydroxycarbonylnaphtho[1,2-c]furan-3(1H)-one in dry MeOH (15 mL) was added TsOH (150 mg) and CH(OMe)3 (0.5 mL). The mixture was stirred at reflux for 2 h. The mixture was then cooled to rt, diluted with saturated aqueous NaHCO3, acidified with AcOH and extracted with EtOAc. The extract was dried over MgSO4 and concentrated in vacuo. The crude material was chromatographed on silica gel (85:15:1 to 66:33:1 hexanes:EtOAc:AcOH) to give the title compound (120 mg, 79% from 1-hydroxy-6-hydroxycarbonylnaphtho[1,2-c]furan-3(1H)-one).

Workup

  1. temperatureat reflux for 2 h
  2. extractionextracted with EtOAc
  3. dry with materialThe extract was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude material was chromatographed on silica gel (85:15:1 to 66:33:1 hexanes:EtOAc:AcOH)

Sources & evidence

ORD record
ord-8cae6f6ab9d4451081ece945d7ad2afd
Source dataset
uspto-grants-2003_06
Patent number
US06576766B1

Reaction notes

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