Methanol → 1,6-dimethoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

HRID 19547

Reaction equation

HRID 19547 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].[CH3:24][OH:25]>[N+]([O-])([O-])=O.[Ag+]>[CH2:1]([O:3][C:4]([C:6]1[CH:7]([O:25][CH3:24])[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 887MethanolHCID 686984701-bromo-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

Product 1

HCID 116884041,6-dimethoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl esterYield 24%

Reagents, catalysts & solvents 1

HCID 24470Silver NitrateCatalyst

Procedure

1-Bromo-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (60 mg, 0.18 mmol) obtained in Step 1 was dissolved in methanol (10 mL), silver nitrate (37.20 mg, 0.22 mmol) was added thereto, stirred for 3 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 14 mg of the titled compound (yield: 24%).

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-1046f77f00fd4ad4b67f07f851c18159
Source dataset
uspto-grants-2010_06
Patent number
US07745439B2

Linked notes

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