Acetone → HCID 10568125, compound

HRID 1108291Notes

Reaction equation

HRID 1108291 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([C:7]2[O:17][C:16]3[CH:15]=[C:14]([OH:18])[CH:13]=[C:12]([OH:19])[C:11]=3[C:9](=[O:10])[C:8]=2[OH:20])=[CH:5][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][CH3:29].[CH3:30][C:31](C)=O>>[CH2:30]([O:20][C:8]1[C:9](=[O:10])[C:11]2[C:16](=[CH:15][C:14]([O:18][CH2:28][CH3:29])=[CH:13][C:12]=2[OH:19])[O:17][C:7]=1[C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1)[CH3:31]

Participants

5

Reactant 4

HCID 180AcetoneHCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 5281616Galangin

Product 1

HCID 10568125HCID 10568125, compoundYield 64%

Procedure

Galangin (27 mg, 0.1 mmol) was dissolved in dried acetone (20 mL), solid potassium carbonate (0.5 g) and bromoethane (1 mL) were added and the mixture was stirred overnight, at room temperature. The solution was filtered and evaporated, water (20 mL) and concentrated ammonium hydroxide (2 mL) were added and the solution was extracted with ethyl acetate (20 mL×2). The solution was dried and the solvent was evaporated. The residue was purified by preparative TLC plate (silica, ethyl acetate/petroleum ether 2:8) to give 21 mg product (64%). 1HNMR (CDCl3): d 1.34 (t, 3H, J=7.3 Hz, 3-CH3), 1.48 (t, 3H, J=7.1 Hz, 7-CH3), 4.14 (m, 4H, 2×OCH2), 6.38 (s, 1H, 6-H), 6.47 (s, 1H, 8-H), 12.64 (s, 1H, 5-OH). MS (CI/NH3): m/z 327 (MH+, base).

Workup

  1. filtrationThe solution was filtered
  2. customevaporated
  3. additionwater (20 mL) and concentrated ammonium hydroxide (2 mL) were added
  4. extractionthe solution was extracted with ethyl acetate (20 mL×2)
  5. customThe solution was dried
  6. customthe solvent was evaporated
  7. customThe residue was purified by preparative TLC plate (silica, ethyl acetate/petroleum ether 2:8)

Sources & evidence

ORD record
ord-f2434b6e0095477eb119c939edef6c34
Source dataset
uspto-grants-2000_05
Patent number
US06066642

Reaction notes

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