Water → HCID 23286094, compound

HRID 369369Notes

Reaction equation

HRID 369369 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([CH3:20])[O:19]CCO2)=[CH:11][C:10]=1[CH2:21][CH2:22][OH:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:19])[CH3:20])=[CH:11][C:10]=1[CH2:21][CH2:22][O:23][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 23286089HCID 23286089, compound

Product 1

HCID 23286094HCID 23286094, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-[2-Benzyloxy-5-(2-methyl-1,3-dioxolan-2-yl)phenyl]ethanol (9.0 g) was dissolved in N,N-dimethylformamide (100 ml), and 60% sodium hydride in oil (1.26 g) was added to the solution under ice-cooling with stirring. After reaction for an hour at room temperature, benzyl bromide (3.75 ml) was added to the reaction mixture under ice-cooling with stirring, followed by reaction for 16 hours at room temperature. Ice (100 g) and water (100 ml) were added to the reaction mixture, and the resulting mixture was extracted with diethyl ether, then the solvent was removed in vacuo. The residue was dissolved in 1,2-dimethoxyethane (50 ml), and 1 N hydrochloric acid (10 ml) was added to the solution, then the resulting mixture was stirred for 30 minutes at room temperature. Water was added to the reaction mixture, and the resulting mixture was extracted with diethyl ether. The extract was dried over anhydrous magnesium sulfate, and the solvent was removed in vacuo. Purification of the residue by medium pressure liquid column chromatography on silica gel (eluent: hexane/diethyl ether=2/1) gave 4'-benzyloxy-3'-(2-benzyloxyethyl)acetophenone (8.5 g) as an oil.

Workup

  1. temperaturecooling
  2. customAfter reaction for an hour at room temperature
  3. temperaturecooling
  4. stirringwith stirring
  5. customfollowed by reaction for 16 hours at room temperature
  6. extractionthe resulting mixture was extracted with diethyl ether
  7. customthe solvent was removed in vacuo
  8. dissolutionThe residue was dissolved in 1,2-dimethoxyethane (50 ml)
  9. addition1 N hydrochloric acid (10 ml) was added to the solution
  10. stirringthe resulting mixture was stirred for 30 minutes at room temperature
  11. additionWater was added to the reaction mixture
  12. extractionthe resulting mixture was extracted with diethyl ether
  13. dry with materialThe extract was dried over anhydrous magnesium sulfate
  14. customthe solvent was removed in vacuo
  15. customPurification of the residue by medium pressure liquid column chromatography on silica gel (eluent: hexane/diethyl ether=2/1)

Sources & evidence

ORD record
ord-c95ac264e4a04865bb2a4f7fe36ac5bf
Source dataset
uspto-grants-2000_10
Patent number
US06136852

Reaction notes

Loading…