Tetrahydrofuran → 1-hydroxy-6-methoxy-1,3-diphenyl-1H-indene-2-carboxylic acid ethyl ester

HRID 19523

Reaction equation

HRID 19523 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH:5]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17](OC)[CH:16]=1)[C:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].[C:24]1([Mg]Cl)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1C[O:35][CH2:34]C1>>[CH2:1]([O:3][C:4]([C:5]1[C:6]([OH:13])([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:24]2[C:29]([C:14]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[CH:28][CH:27]=[C:26]([O:35][CH3:34])[CH:25]=2)=[O:23])[CH3:2]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 118449532-(3-Methoxy-benzyl)-3-oxo-3-phenyl-propionic acid ethyl esterHCID 178478979HCID 178478979, compound

Product 1

HCID 115961681-hydroxy-6-methoxy-1,3-diphenyl-1H-indene-2-carboxylic acid ethyl esterYield 76%

Conditions

Temperature
0 °C

Procedure

The compound (300 mg, 0.97 mmol) obtained in Step 1 was dissolved in THF and 1.5 equivalents of phenylmagnesium chloride were added thereto, followed by stirring for 1 hr at 0° C. Then, the resulting mixture washed with saturated saline, and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous MgSO4, and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 285 mg of the titled compound (yield: 76%).

Workup

  1. washThen, the resulting mixture washed with saturated saline
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated under a reduced pressure
  6. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-6752d39a677c4ee1b9821a25bdb58aaf
Source dataset
uspto-grants-2010_06
Patent number
US07745439B2

Linked notes

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