Hydrochloric Acid → HCID 19369861, compound

HRID 849032Notes

Reaction equation

HRID 849032 reaction equation
[OH-].[Na+].C([O:6][C:7]1[C:8]([O:22][CH3:23])=[C:9]([O:20][CH3:21])[C:10]2[O:14][C:13]([CH2:16][Br:17])([CH3:15])[CH2:12][C:11]=2[C:18]=1[CH3:19])(=O)C.Cl>CO>[Br:17][CH2:16][C:13]1([CH3:15])[CH2:12][C:11]2[C:18]([CH3:19])=[C:7]([OH:6])[C:8]([O:22][CH3:23])=[C:9]([O:20][CH3:21])[C:10]=2[O:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19369854HCID 19369854, compound

Product 1

HCID 19369861HCID 19369861, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An aqueous 2.5N sodium hydroxide solution (20 ml) was added to a solution (20 ml) of 5-acetoxy-2-bromomethyl-2,3-dihydro-6,7-dimethoxy-2,4-dimethylbenzofuran (2.5 g) in methanol (20 ml), and the mixture was stirred under an atmosphere of argon at room temperature for 1 hour. The reaction mixture was made acidic with 3N hydrochloric acid, and then extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=85:15) to obtain the title compound (1.9 g, 87%) as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=85:15)

Sources & evidence

ORD record
ord-b0dde6cf72c84c8e824859b4ec393f49
Source dataset
uspto-grants-2000_01
Patent number
US06011046

Reaction notes

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