Reaktion #81730

Reaktionsgleichung

NaCl

17β-(3,4-methylenedioxybenzoyl)-estra-1,3,5(10)-triene-3-carboxaldehyde

2-methyl-2-butene

NaClO2

→

title compound

Ausbeute 47.0%

17β-(3,4-Methylenedioxybenzoyl)-estra-1,3,5(10)-triene-3-carboxylic acid

Ausbeute 47.0%

Lösungsmittel

Acetic acid

tert-butyl alcohol

H2O

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionwas extracted with EtOAc
2. 2
   WaschenThe organic layer was washed with H2O, brine
3. 3
   Trocknendried (MgSO4)
4. 4
   Einengenconcentrated and azetroped with toluene
5. 5
   SonstigeThe resulting solid was triturated with CH3CN- acetone
6. 6
   Filtrationfiltered

Vorschrift

To a stirred mixture of 17β-(3,4-methylenedioxybenzoyl)-estra-1,3,5(10)-triene-3-carboxaldehyde (0.041 g, 0,1 mmoles), tert-butyl alcohol (1.05 mL), 2-methyl-2-butene (4 mL of 2M solution in THF, 8 mmoles) at 0° C. was added a solution of NaClO2 (9 mg, 0.1 mmoles) and NaH2PO4. H2O (0.137 g, 0.1 mmoles) in H2O (0.4 ml) and stirred for 2 hours at ambient temperature. Acetic acid (glacial, 0.8 ml) and saturated NaCl solution (1.3 mL) were added to the reaction mixture which was extracted with EtOAc. The organic layer was washed with H2O, brine, dried (MgSO4), concentrated and azetroped with toluene. The resulting solid was triturated with CH3CN- acetone and filtered to give 0.02 g (47%) of the title compound as a white solid, mp 235°-237° C.

Quelle