Ethanol → HCID 66685791, compound

HRID 922265Notes

Reaction equation

HRID 922265 reaction equation
O1CCCC1.[CH3:6][C:7]1[C:11]([C:12]2[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:13]=2[CH2:19][CH2:20][C:21]([O:23]CC)=[O:22])=[C:10]([CH3:26])[O:9][N:8]=1.CCO.[OH-].[Na+]>O>[CH3:6][C:7]1[C:11]([C:12]2[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:13]=2[CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[C:10]([CH3:26])[O:9][N:8]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66685850HCID 66685850, compound

Product 1

HCID 66685791HCID 66685791, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 10 mL RB flask fitted with magnetic stirrer was charged with 3 mL of tetrahydrofuran. To the stirred solvent were added ethyl 3-[2-(3,5-dimethyl-1,2-oxazol-4-yl)-4-hydroxy phenyl]propanoate (0.10 g, 0.35 mmol), ethanol (3 mL) and sodium hydroxide (0.015 g, 0.0.35 mmol) in water (0.5 mL). The reaction mixture was stirred at room 16 h. After completion of the reaction, the solvent was removed, the sodium salt was washed with diethyl ether (5 mL); the aqueous layer was acidified with 1N HCl to pH 2.0 and extracted with ethyl acetate (5 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure to obtain the product (0.04 g, yield: 44.4%).

Workup

  1. customTo a 10 mL RB flask fitted with magnetic stirrer
  2. customAfter completion of the reaction
  3. customthe solvent was removed
  4. washthe sodium salt was washed with diethyl ether (5 mL)
  5. extractionextracted with ethyl acetate (5 mL)
  6. dry with materialThe organic layer was dried over anhydrous Na2SO4
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-438fa500d7e742618fa904776abd3756
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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