Sodium hydride → HCID 66770868, compound

HRID 1697762Notes

Reaction equation

HRID 1697762 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:28])[CH:6]([O:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)[CH2:7][CH2:8]OS(C1C=CC(C)=CC=1)(=O)=O>COCCOC>[CH3:3][O:4][C:5]([C:6]1([O:20][C:21]2[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=2)[CH2:7][CH2:8]1)=[O:28]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86646873HCID 86646873, compound

Product 1

HCID 66770868HCID 66770868, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
22 °C

Procedure

A suspension of sodium hydride in oil (55% w/w, 36.4 mg) was added to a solution of 2-(4-Chloro-phenoxy)-4-(toluene-4-sulfonyloxy)-butyric acid methyl ester (Example 473c), 145 mg) in 1,2-dimethoxyethane (2.27 mL) at room temperature. The mixture was stirred at 22° C. for 48 hr. The reaction mixture was filtered and the solid was washed with ethyl acetate. Water was added to the filtrate. The phases were separated and the aqueous layer was extracted with ethylacetate. The organic layers were washed with brine, dried over sodium sulfate and filtered. The crude mixture was concentrated to dryness and purified by chromatography on silica gel to yield the title compound as a colorless oil (56 mg; 68%). MS (ESI): m/z=226 [M]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solid was washed with ethyl acetate
  3. additionWater was added to the filtrate
  4. customThe phases were separated
  5. extractionthe aqueous layer was extracted with ethylacetate
  6. washThe organic layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationThe crude mixture was concentrated to dryness
  10. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-dbd89d444bf042a09ccce7e428459765
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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