反応 #81730

反応方程式

NaCl

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

2-methyl-2-butene

NaClO2

→

title compound

収率 47.0%

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

収率 47.0%

溶媒

Acetic acid

tert-butyl alcohol

H2O

H2O

反応条件

後処理

1. 1
   抽出was extracted with EtOAc
2. 2
   洗浄The organic layer was washed with H2O, brine
3. 3
   乾燥dried (MgSO4)
4. 4
   濃縮concentrated and azetroped with toluene
5. 5
   その他The resulting solid was triturated with CH3CN- acetone
6. 6
   ろ過filtered

実験手順

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.

出典