Sodium Acetate → HCID 10636944, compound

HRID 579949Notes

Reaction equation

HRID 579949 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[Na+].CS(O[C@H:11]([CH3:27])[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:16][CH:15]=1)(=O)=O>CN(C)C=O>[C:1]([O:4][C@@H:11]([CH3:27])[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:16][CH:15]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 15671700HCID 15671700, compound

Product 1

HCID 10636944HCID 10636944, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of anhydrous sodium acetate (82 mg, 1.0 mmol), (R)-1-methyl-2-(4-phenoxyphenoxy)ethyl methanesulfonate (250 mg, 0.78 mmol; ee.: 99.4%) and dimethylformamide (5 ml) was stirred at an inner temperature of 100° to 110° C. for 5 hours. After allowed to cool, ice-water was added thereto, and the reaction mixture was extracted with toluene three times. The toluene layer was dried over anhydrous magnesium sulfate. The solvent was removed, and the residue was purified by thin layer chromatography using silica gel to give (S)-(-)-1-methyl-2-(4- phenoxyphenoxy)ethyl acetate (158 mg). [α]D23 =-30.6° (CHCl3, c=1). ee.: 88.8%.

Workup

  1. temperatureto cool
  2. extractionthe reaction mixture was extracted with toluene three times
  3. dry with materialThe toluene layer was dried over anhydrous magnesium sulfate
  4. customThe solvent was removed
  5. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-236e821700fd4a9e908e79bbe4893fb7
Source dataset
uspto-grants-1988_06
Patent number
US04751225

Reaction notes

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