Sodium Methoxide → HCID 131727250, compound

HRID 1454790Notes

Reaction equation

HRID 1454790 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[CH:10]1[CH2:19][CH2:18][C:13]2([O:17][CH2:16][CH2:15][O:14]2)[CH2:12][CH:11]1[C:20]([O-:22])=[O:21].[CH3:23][O-].[Na+]>CO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C@@H:10]1[CH2:19][CH2:18][C:13]2([O:14][CH2:15][CH2:16][O:17]2)[CH2:12][C@H:11]1[C:20]([O:22][CH3:23])=[O:21]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 131727251HCID 131727251, compound

Product 1

HCID 131727250HCID 131727250, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 8-(2,4,5-trifluorophenyl)-1,4-dioxaspiro[4.5]decane-7-carboxylate (1.95 g, 5.9 mmol) in methanol (50 mL) was added sodium methoxide (0.5M in methanol, 14.2 ml, 7.1 mmol), and the resulting solution was refluxed overnight under a nitrogen atmosphere, cooled to room temperature and evaporated to yield the crude product which was purified by chromatography on a Biotage® system (silica gel, ethyl acetate in hexanes gradient 25-54%) to yield the title compound containing some cis isomer.

Workup

  1. temperaturethe resulting solution was refluxed overnight under a nitrogen atmosphere
  2. customevaporated
  3. customto yield the crude product which
  4. customwas purified by chromatography on a Biotage® system (silica gel, ethyl acetate in hexanes gradient 25-54%)

Sources & evidence

ORD record
ord-be1b2f6385054496b46380fc07871a17
Source dataset
uspto-grants-2009_01
Patent number
US07482336B2

Reaction notes

Loading…