HCID 10559780, compound → HCID 10511296, compound

HRID 1033093Notes

Reaction equation

HRID 1033093 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6](=[O:14])[CH2:7][CH2:8][C:9]([O:11]CC)=[O:10])=[CH:2]1>CO.O.C1COCC1.[OH-].[Na+]>[O:1]1[CH:5]=[CH:4][C:3]([C:6](=[O:14])[CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:2]1

Participants

4

Reactant 1

HCID 10559780HCID 10559780, compound

Product 1

HCID 10511296HCID 10511296, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

The keto ester from Step 1 (38.9 g, 0.193 mmoL) was dissolved in a mixture of MeOH:H2O:THF (3:1:2) (150 mL) and NaOH 1N (213 mL, 0.213 mmoL) was added. The reaction was stirred at r.t. overnight. The mixture was concentrated, acidified with HCl 1N extracted (2×) with EtOAc, washed with brine, dried over MgSO4, filtered and evaporated to afford the title product as a beige solid.

Workup

  1. additionwas added
  2. concentrationThe mixture was concentrated
  3. extractionextracted (2×) with EtOAc
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-a9701c3d113e4c249c90cb01a44703ab
Source dataset
uspto-grants-1994_05
Patent number
US05308852

Reaction notes

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