Sodium Hydroxide → 1-benzyl-1-hydroxy-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid

HRID 19543Notes

Reaction equation

HRID 19543 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([OH:23])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)=[O:5])C.[OH-].[Na+]>C1COCC1.C(O)C>[CH2:24]([C:7]1([OH:23])[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)[C:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[C:6]1[C:4]([OH:5])=[O:3])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 115675291-benzyl-1-hydroxy-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

Product 1

HCID 116464291-benzyl-1-hydroxy-6-methoxy-3-phenyl-1H-indene-2-carboxylic acidYield 108%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-Benzyl-1-hydroxy-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (35 mg, 0.087 mmol) prepared in Example 5 was dissolved in THF, and an excess amount of sodium hydroxide dissolved in aqueous ethanol was added thereto in such a way not to cause layer separation. The mixture was stirred for 24 hrs at RT, and the pH was adjusted to 3˜4 using 2N hydrochloric acid. The resulting mixture was extracted with ethyl acetate. The organic layer was separated, dried over anhydrous MgSO4 and concentrated under a reduced pressure, to obtain 35 mg of the titled compound (yield: 100%).

Workup

  1. additionwas added
  2. customlayer separation
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-0c7daac6a459421fb27a5325de6421cc
Source dataset
uspto-grants-2010_06
Patent number
US07745439B2

Reaction notes

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