HCID 71093203, compound → 3193-25-7

HRID 1472742Notes

Reaction equation

HRID 1472742 reaction equation
[OH:1][C:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:8]1[CH:12]=[CH:11][S:10][CH:9]=1)[C:3]([O:5]CC)=[O:4]>C1COCC1.[OH-].[Na+]>[OH:1][C:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:8]1[CH:12]=[CH:11][S:10][CH:9]=1)[C:3]([OH:5])=[O:4]

Participants

4

Reactant 1

HCID 71093203HCID 71093203, compound

Product 1

HCID 2885133193-25-7Yield 79.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of ethyl 2-hydroxy-2-phenyl-2-(thiophen-3-yl)acetate (1.06 g, 4.02 mmol) in THF (10 mL), sodium hydroxide (10 mL, 2.0 M aqueous solution) was added. The reaction was heated at 60° C. for 24 hours. The reaction was allowed to cool to RT, and THF was removed under reduced pressure. The resultant residue was washed with diethyl ether (×3). The aqueous layer was acidified to pH 1 with 2.0 M aqueous hydrochloric acid and extracted with ethyl acetate (×3). The combined ethyl acetate layers were washed with saturated sodium chloride solution, dried (magnesium sulfate), filtered and concentrated in vacuo to afford the title compound (0.75 g, 79%).

Workup

  1. temperatureto cool to RT
  2. customTHF was removed under reduced pressure
  3. washThe resultant residue was washed with diethyl ether (×3)
  4. extractionextracted with ethyl acetate (×3)
  5. washThe combined ethyl acetate layers were washed with saturated sodium chloride solution
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c26ce9f7c4549bc9bc5b2c021d958d8
Source dataset
uspto-grants-2015_04
Patent number
US09012644B2

Reaction notes

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