Sodium Hydroxide → HCID 67643754, compound

HRID 399203Notes

Reaction equation

HRID 399203 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 NaCi 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 NaCi
  4. customdried
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8da4e535beae45bfb817e42b7e88a7a5
Source dataset
uspto-grants-1998_10
Patent number
US05817693

Reaction notes

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