Sodium hydride → HCID 86644716, compound

HRID 453769Notes

Reaction equation

HRID 453769 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([OH:18])=[C:13]([C:15](=[O:17])[CH3:16])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].CC1C=CC(S(O[CH2:32][C@H:33]2[CH2:35][O:34]2)(=O)=O)=CC=1>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:18][CH2:32][C@H:33]2[CH2:35][O:34]2)=[C:13]([C:15](=[O:17])[CH3:16])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 154187Glycidyl tosylate, (R)-HCID 128709281-[5-(Benzyloxy)-2-hydroxyphenyl]ethan-1-one

Product 1

HCID 86644716HCID 86644716, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of 1-(5-benzyloxy-2-hydroxyphenyl)ethanone (3.0 g, 12.4 mmol) in anhydrous DMF (15 ml) was added NaH (0.55 g, 13.6 mmol). The mixture was allowed to stir at RT for 30 min and then heated to 60° C. A solution of (R)-oxiran-2-ylmethyl 4-methylbenzenesulfonate (2.83 g, 12.4 mmol) in DMF was added dropwise at 60° C. during 1 h. Stirring was then continued at 60° C. for 3 h. The cooled reaction was quenched by addition of water (80 ml) and extracted three times with EtOAc. The combined organic layers were extracted twice with aq 1 M NaOH and washed with water and brine. The organic layer was dried with Na2SO4 and concentrated. The crude product obtained was purified by column chromatography with EtOAc/toluene as eluent to afford the title compound (2.35 g) as a white solid.

Workup

  1. temperatureheated to 60° C
  2. stirringStirring
  3. waitwas then continued at 60° C. for 3 h
  4. customThe cooled reaction
  5. customwas quenched by addition of water (80 ml)
  6. extractionextracted three times with EtOAc
  7. extractionThe combined organic layers were extracted twice with aq 1 M NaOH
  8. washwashed with water and brine
  9. dry with materialThe organic layer was dried with Na2SO4
  10. concentrationconcentrated
  11. customThe crude product obtained
  12. customwas purified by column chromatography with EtOAc/toluene as eluent

Sources & evidence

ORD record
ord-d8e6dbf4ddfc40f5b96641161c894a53
Source dataset
uspto-grants-2013_07
Patent number
US08492549B2

Reaction notes

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