Hydrochloric Acid → HCID 178442265, compound

HRID 567206Notes

Reaction equation

HRID 567206 reaction equation
[C:1]1([C:7]([C:9]2[C:14]([OH:15])=[CH:13][C:12]([OH:16])=[C:11]([OH:17])[C:10]=2[OH:18])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23].[Cl-].[NH4+].Cl>>[CH3:23][C:22]([CH3:24])=[CH:21][CH2:20][C:11]1([OH:17])[C:12]([OH:16])=[C:13]([CH2:3][CH:2]=[C:1]([CH3:7])[CH3:6])[C:14]([OH:15])=[C:9]([C:7](=[O:8])[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:10]1=[O:18]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 104291-Chloro-3-methyl-2-buteneHCID 25517Ammonium ChlorideHCID 21477447HCID 21477447, compound

Product 1

HCID 178442265HCID 178442265, compoundYield 102.3%

Procedure

Under a stream of argon, 440 mg (11.0 mmol, 3.01 equivalents) of an oily dispersion of 60% sodium hydride was washed with hexane to remove the oil component. The dispersion kept cooled with cold water and 18.0 ml of dry dimethyl sulfoxide added were stirred together. To the stirred suspension, 900 mg (3.66 mmol) of phenyl-(2,3,4,6-tetrahydroxyphenyl) ketone (10) was added and stirred for 30 minutes. Further, 0.830 ml (7.32 mmol, 2.00 equivalents) of 1-chloro-3-methyl-2-butene was added dropwise stirring for two hours. The produced mixture was combined with 15 ml of a saturated aqueous ammonium chloride solution and 2 ml of 2 M hydrochloric acid solution and extracted by ether. The organic layer was washed with saturated brine, dried over sodium sulfate, concentrated under a reduced pressure, and subjected to silica gel chromatography (g of Wako Gel C-200, eluted with hexane ethyl acetate 4:1) to obtain 716 mg (yield 51.3%) of the product (32) in the form of yellow powdery crystals.

Workup

  1. washUnder a stream of argon, 440 mg (11.0 mmol, 3.01 equivalents) of an oily dispersion of 60% sodium hydride was washed with hexane
  2. customto remove the oil component
  3. temperatureThe dispersion kept cooled with cold water and 18.0 ml of dry dimethyl sulfoxide
  4. additionadded
  5. stirringstirred for 30 minutes
  6. stirringstirring for two hours
  7. extractionextracted by ether
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated under a reduced pressure
  11. washsubjected to silica gel chromatography (g of Wako Gel C-200, eluted with hexane ethyl acetate 4:1)

Sources & evidence

ORD record
ord-ed80d2e621d04a8d82e0312d3d10b023
Source dataset
uspto-grants-2001_01
Patent number
US06177474B1

Reaction notes

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