Ethanol → 1-ethoxy-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

HRID 19548

Reaction equation

HRID 19548 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7](Br)[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])[CH3:2].[CH2:24]([OH:26])[CH3:25]>[N+]([O-])([O-])=O.[Ag+]>[CH2:1]([O:3][C:4]([C:6]1[CH:7]([O:26][CH2:24][CH3:25])[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])[CH3:2]

Participants

4

Reactant 2

HCID 702EthanolHCID 686984701-bromo-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

Product 1

HCID 116601011-ethoxy-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl esterYield 52%

Reagents, catalysts & solvents 1

HCID 24470Silver NitrateCatalyst

Procedure

1-Bromo-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (30 mg, 0.09 mmol) obtained in Example 18 was dissolved in ethanol (3 mL), silver nitrate (15.50 mg, 0.09 mmol) was added thereto, stirred for 3.5 hrs at RT, and filtered. The organic layer was separated, and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 16 mg of the titled compound (yield: 52%).

Workup

  1. filtrationfiltered
  2. customThe organic layer was separated
  3. concentrationconcentrated under a reduced pressure
  4. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-87633b90324c42a59e3bb02d07e2d09b
Source dataset
uspto-grants-2010_06
Patent number
US07745439B2

Linked notes

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