Tetrahydrofuran → 1-hydroxy-isopropyl-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

HRID 19525

Reaction equation

HRID 19525 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=O)[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].[CH:24]([Mg]Cl)([CH3:26])[CH3:25].C1C[O:32]CC1>>[CH2:1]([O:3][C:4]([C:6]1[CH:7]([C:24]([OH:32])([CH3:26])[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 3

HCID 8028TetrahydrofuranHCID 23249734Ethyl 6-methoxy-1-oxo-3-phenyl-1H-indene-2-carboxylateHCID 178418918HCID 178418918, compound

Product 1

HCID 687025631-hydroxy-isopropyl-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl esterYield 45.2%

Conditions

Temperature
0 °C

Procedure

6-Methoxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (300 mg, 0.974 mmol) obtained in Example 1 was dissolved in THF and 1.5 equivalents of isopropylmagnesium chloride were added thereto, followed by stirring for 1 hr at 0° C. 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. Then, the resulting residue was purified by flash chromatography to obtain 155 mg of the titled compound (yield: 45.2%).

Workup

  1. washThe 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. customThen, the resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-4f635f39a7c54e08a76977b06d31a1b6
Source dataset
uspto-grants-2010_06
Patent number
US07745439B2

Linked notes

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