Benzyl Bromide → HCID 21264715, compound

HRID 567207Notes

Reaction equation

HRID 567207 reaction equation
[OH:1][C:2]1[C:7]([OH:8])=[C:6]([OH:9])[CH:5]=[C:4]([OH:10])[C:3]=1[C:11]([CH2:13][CH:14]([CH3:16])[CH3:15])=[O:12].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>[Cl-].[NH4+]>[CH2:17]([C:7]1([OH:8])[C:6]([OH:9])=[C:5]([CH2:11][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=2)[C:4]([OH:10])=[C:3]([C:11](=[O:12])[CH2:13][CH:14]([CH3:16])[CH3:15])[C:2]1=[O:1])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 14446594HCID 14446594, compound

Product 1

HCID 21264715HCID 21264715, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

Under a stream of argon, 212 mg (5.31 mmol, 2.40 equivalents) of an oily dispersion of 60% sodium hydride was washed with hexane to remove the oil component. While the dispersion kept cooled with cold water, 11.0 ml of dry dimethyl sulfoxide was added and stirred. To this, was added 500 mg (2.21 mmol) of 2-methylpropyl-(2,3,4,6-tetrahydroxyphenyl) ketone (9) and stirred for 40 minutes. To the produced mixture, 0.525 ml (4.42 mmol, 2.00 equivalents) of benzyl bromide was added dropwise and stirred for four hours. The resultant mixture was combined with 10 ml of a saturated aqueous ammonium chloride 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 (100 g of Wako Gel C-200, eluted with hexane:ethyl acetate=3:2) to obtain 207 mg (yield 23.1%) of the product (33) in the form of yellow powdery crystals.

Workup

  1. washUnder a stream of argon, 212 mg (5.31 mmol, 2.40 equivalents) of an oily dispersion of 60% sodium hydride was washed with hexane
  2. customto remove the oil component
  3. temperatureWhile the dispersion kept cooled with cold water, 11.0 ml of dry dimethyl sulfoxide
  4. additionwas added
  5. stirringstirred for 40 minutes
  6. stirringstirred for four 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 (100 g of Wako Gel C-200, eluted with hexane:ethyl acetate=3:2)

Sources & evidence

ORD record
ord-7f11eda5deb24cc183c2f2e70eb9f966
Source dataset
uspto-grants-2001_01
Patent number
US06177474B1

Reaction notes

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