Sodium hydride → (S)-3-[4-(2-Methoxyethyl)phenoxy]-1,2-epoxypropane

HRID 47670

Reaction equation

HRID 47670 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.CC1C=CC(S(O[CH2:23][C@H:24]2[O:26][CH2:25]2)(=O)=O)=CC=1.[H-].[Na+]>CN(C=O)C>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:23][C@@H:24]2[CH2:25][O:26]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 925164-(2-Methoxyethyl)phenolHCID 153296Oxiranemethanol, 4-methylbenzenesulfonate, (S)-

Product 1

HCID 10976684(S)-3-[4-(2-Methoxyethyl)phenoxy]-1,2-epoxypropane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(2-methoxyethyl)phenol (42 mg, 0.275 mmol) and (2S)-(+)-glycidyl tosylate (57 mg, 0.25 mmol) in 2 mL of DMF was added 15 mg (0.625 mmol) of sodium hydride (60% in mineral oil). The resulting mixture was allowed to stir for 16 hours at room temperature. The solution was then extracted three times with ethyl acetate, and the organic phase was washed sequentially with sodium hydroxide, water and brine, dried over sodium sulfate, and concentrated in vacuo to provide the product which was used without further purification. m/z 208 [M+H]+.

Workup

  1. extractionThe solution was then extracted three times with ethyl acetate
  2. washthe organic phase was washed sequentially with sodium hydroxide, water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto provide the product which
  6. customwas used without further purification

Sources & evidence

ORD record
ord-915b532ef5aa4c6983c86cbc722a0c1a
Source dataset
uspto-grants-2004_03
Patent number
US06699860B2

Linked notes

Loading…