تفاعل #42504

ord-eb34d9a2febf4f50a8347ec62a9712ae

معادلة التفاعل

CCCCOC(=O)c1ccc2c(C(=O)C(F)(F)F)cn(CCCC)c2c1
Butyl 1-butyl-3-(trifluoroacetyl)-1H-indole-6-carboxylate
O.[Li][OH]
LiOH.H2O
C1CCOC1
THF
O
water
CCCCn1cc(C(=O)C(F)(F)F)c2ccc(C(=O)O)cc21
1-butyl-3-(trifluoroacetyl)-1H-indole-6-carboxylic acid
المردود 70.7%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىThe solvents were then removed under reduced pressure and HCl (2N, 0.5 mL)
  2. 2
    workup.ADDITIONwas added to the residue
  3. 3
    استخلاصThe residue was extracted with ethyl acetate
  4. 4
    تجفيفdried over magnesium sulfate
  5. 5
    ترشيحfiltered
  6. 6
    تركيزconcentrated

الإجراء التجريبي

Butyl 1-butyl-3-(trifluoroacetyl)-1H-indole-6-carboxylate (0.277 g), LiOH.H2O (0.040 g), THF (1.5 mL), water (0.5 mL), and methanol (0.5 mL) were stirred overnight at room temperature. The solvents were then removed under reduced pressure and HCl (2N, 0.5 mL) was added to the residue. The residue was extracted with ethyl acetate, dried over magnesium sulfate, filtered, and concentrated. Chromatography on silica gel using methanol/dichloromethane (6/94) gave 1-butyl-3-(trifluoroacetyl)-1H-indole-6-carboxylic acid (0.166 g). MS (ESI+) for C15H14F3N1O3+H1 m/z 314.10 (M+H)+.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07727997B2uspto-grants-2010_06