Reaktion #47803

ord-4f635f39a7c54e08a76977b06d31a1b6

Reaktionsgleichung

CCOC(=O)C1=C(c2ccccc2)c2ccc(OC)cc2C1=O
6-Methoxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester
C1CCOC1
THF
C[CH](C)[Mg][Cl]
isopropylmagnesium chloride
CCOC(=O)C1=C(c2ccccc2)c2ccc(OC)cc2C1C(C)(C)O
titled compound
Ausbeute 45.2%
CCOC(=O)C1=C(c2ccccc2)c2ccc(OC)cc2C1C(C)(C)O
1-hydroxy-isopropyl-6-methoxy-3-phenyl-1H-indene-2-carboxylic Acid Ethyl Ester
Ausbeute 45.2%

Reaktionsbedingungen

Temperatur
0°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    WaschenThe resulting mixture washed with saturated saline
  2. 2
    Extraktionextracted with ethyl acetate
  3. 3
    SonstigeThe organic layer was separated
  4. 4
    Trocknendried over anhydrous MgSO4
  5. 5
    Einengenconcentrated under a reduced pressure
  6. 6
    SonstigeThen, the resulting residue was purified by flash chromatography

Vorschrift

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%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07745439B2uspto-grants-2010_06