Water → HCID 23286079, compound

HRID 369427Notes

Reaction equation

HRID 369427 reaction equation
[CH2:1]([O:8][C:9]1[CH:28]=[CH:27][C:12]([C:13]2[O:14][C:15]3[C:20]([C:21](=[O:23])[CH:22]=2)=[CH:19][C:18]([C:24]([OH:26])=[O:25])=[CH:17][CH:16]=3)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:31](I)[CH3:32].O>CN(C)P(N(C)C)(N(C)C)=O>[CH2:1]([O:8][C:9]1[CH:28]=[CH:27][C:12]([C:13]2[O:14][C:15]3[C:20]([C:21](=[O:23])[CH:22]=2)=[CH:19][C:18]([C:24]([O:26][CH2:31][CH3:32])=[O:25])=[CH:17][CH:16]=3)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 10785497HCID 10785497, compound

Product 1

HCID 23286079HCID 23286079, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

4'-Benzyloxy-6-carboxyflavone (1 eq.) was dissolved in HMPA (hexamethylphosphoramide), followed by the addition of sodium hydride (1.1 eq.). Thirty minutes later, ethyl iodide (2 eq.) was added, and the resulting mixture was stirred further for 2 hours at room temperature. The mixture was charged into water, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, whereby the title compound represented by the following formula was obtained (yield: 25%). ##STR18##

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure, whereby the title compound
  5. customwas obtained (yield: 25%)

Sources & evidence

ORD record
ord-be6ef8604c464a9bbcb41a4e808481d4
Source dataset
uspto-grants-2000_10
Patent number
US06136848

Reaction notes

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