Lithium Hydroxide → HCID 21713168, compound

HRID 650709Notes

Reaction equation

HRID 650709 reaction equation
C[O:2][C:3](=[O:18])/[C:4](/[CH2:15][CH2:16][CH3:17])=[CH:5]/[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7].[OH-].[Li+]>C1COCC1.O>[C:9]1([S:6](/[CH:5]=[C:4](\[CH2:15][CH2:16][CH3:17])/[C:3]([OH:18])=[O:2])(=[O:8])=[O:7])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 70244124HCID 70244124, compound

Product 1

HCID 21713168HCID 21713168, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

(E)-3-benzenesulfonyl-2-propylacrylic acid methyl ester (5.0 g, 16.84 mmol) was dissolved in THF/water 3:1 (20 ml). Lithium hydroxide (0.86 g, 20.49 mmol) was added and the solution was stirred at room temperature overnight. The solvent was evaporated and the mixture was partitioned between ethyl acetate (50 ml) and water (40 ml). The aqueous layer was acidifed with 2M H2SO4 (6 ml) and the product was extracted into ethyl acetate (2×30 ml). The combined organic layers were washed with 2M H2SO4 (20 ml), brine, dried over magnesium sulfate, filtered and evaporated to give the title compound in 83% yield.

Workup

  1. customThe solvent was evaporated
  2. customthe mixture was partitioned between ethyl acetate (50 ml) and water (40 ml)
  3. extractionthe product was extracted into ethyl acetate (2×30 ml)
  4. washThe combined organic layers were washed with 2M H2SO4 (20 ml), brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-697cad24739444a995eb371c53fa8a53
Source dataset
uspto-grants-2001_08
Patent number
US06274758B1

Reaction notes

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