Sodium Hydroxide → HCID 67643754, compound

HRID 863110Notes

Reaction equation

HRID 863110 reaction equation
[O:1]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[CH:16]2[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:11][CH:10]=1)[Si](C(C)(C)C)(C)C.[OH-].[Na+]>CCO>[OH:1][C:9]1[CH:10]=[CH:11][C:12]([CH:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[CH:16]2[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67643210HCID 67643210, compound

Product 1

HCID 67643754HCID 67643754, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl (1RS,2SR,3SR)-1-(4-t-butyldimethylsiloxyphenyl)-3-(4-methoxyphenyl)indane-2-carboxylate (723 mg, 1.4 mmol) in EtOH (20 ml) was added 1M NaOH (1.6 ml, 1.6 mmol), and the resulting mixture was stirred at room temperature for 30 min. The mixture was then partitioned between 3M HCl and EtOAc. The aqueous phase was extracted with EtOAc, and the combined organic extracts were washed successively with H2O and saturated aqueous NaCl and dried. The solvent was removed in vacuo to afford the title compound (554 mg, 100%).

Workup

  1. customThe mixture was then partitioned between 3M HCl and EtOAc
  2. extractionThe aqueous phase was extracted with EtOAc
  3. washthe combined organic extracts were washed successively with H2O and saturated aqueous NaCl
  4. customdried
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-20f02300378e4230b9551242c5a64638
Source dataset
uspto-grants-1998_02
Patent number
US05719183

Reaction notes

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