Hydrochloric Acid → HCID 67643887, compound

HRID 862916Notes

Reaction equation

HRID 862916 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[CH:9]2[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:4][CH:3]=1.N1C=CN=C1.[C:28]([Si:32]([CH3:35])([CH3:34])Cl)([CH3:31])([CH3:30])[CH3:29].Cl>CN(C=O)C>[O:1]([C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[CH:9]2[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:6][CH:7]=1)[Si:32]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:35])[CH3:34]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 67643022HCID 67643022, compound

Product 1

HCID 67643887HCID 67643887, compoundYield 128.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl(2RS,3SR)-3-(4-hydroxyphenyl)-1-oxoindane-2-carboxylate (3.0 g, 10.2 mmol) in DMF (10 ml) under an argon atmosphere were added imidazole (1.72 g, 25.3 mmol) and t-butyldimethylchloro-silane (1.82 g, 12.1 mmol). The resulting mixture was allowed to stir at room temperature for 3 d, then was poured into dilute aqueous HCl and extracted with EtOAc (2×). The combined organic extracts were washed successively with H2O, aqueous NaHCO3, H2O and saturated aqueous NaCl and dried. The solvent was removed in vacuo to provide the title compound (5.40 g) which was used without further purification.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic extracts were washed successively with H2O, aqueous NaHCO3, H2O and saturated aqueous NaCl
  3. customdried
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-42e746b80c4d4a599919538f1ca891db
Source dataset
uspto-grants-1998_02
Patent number
US05719182

Reaction notes

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