Sodium hydride → (RS)-4-(Ethylthio)-2-phenylbutanoic Acid

HRID 1077416Notes

Reaction equation

HRID 1077416 reaction equation
Br[CH2:2][CH2:3][CH:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:5]([OH:7])=[O:6].[H-].[Na+].[Na].[CH2:17]([SH:19])[CH3:18]>CN(C)C=O>[CH2:17]([S:19][CH2:2][CH2:3][CH:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:5]([OH:7])=[O:6])[CH3:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 167406054-Bromo-2-phenylbutanoic acidHCID 45051917HCID 45051917, compound

Product 1

HCID 19431596(RS)-4-(Ethylthio)-2-phenylbutanoic AcidYield 89.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

(RS)-4-Bromo-2-phenylbutanoic acid (prepared as described in Farmaco (pavia) Ed. Sci. 355 21(5) 1966) (2.43 g) in dimethylformamide (5 ml) was added to a stirred suspension of sodium hydride (0.33 g, as an 80% dispersion in oil) and ethanethiol sodium salt (1.26 g) in dimethylformamide (15 ml) at 0° C. The mixture was warmed to room temperature, stirred for 2 hours and evaporated. The residue was partitioned between water and ethylacetate, the aqueous layer acidified with concentrated hydrochloric acid and extracted with ethylacetate. The organic layer was dried over sodium sulphate and evaporated to give the title compound (2 g, 89%) as an oil.

Workup

  1. customat 0° C
  2. customevaporated
  3. customThe residue was partitioned between water and ethylacetate
  4. extractionextracted with ethylacetate
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-8162c738286a4d6480c2543397cfdb54
Source dataset
uspto-grants-1996_08
Patent number
US05543419

Reaction notes

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