Diethyl Ether → HCID 24853388, compound

HRID 500526Notes

Reaction equation

HRID 500526 reaction equation
[C:1]1([CH3:14])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[O:11][N:10]=[C:9]([CH:12]=[O:13])[CH:8]=2)[CH:2]=1.[CH3:15][Mg]Br.C(OCC)C>C1COCC1>[CH3:14][C:1]1[CH:2]=[C:3]([C:7]2[O:11][N:10]=[C:9]([CH:12]([OH:13])[CH3:15])[CH:8]=2)[CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24853387HCID 24853387, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 24853388HCID 24853388, compoundYield 103.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound of Example 5.3 (739 mg, 3.9 mmol) was dissolved in THF (20 mL) under Argon and the flask was immersed in ice. Methyl magnesium bromide (1 M solution/diethyl ether 6.6 mL, 19.7 mmol) was added dropwise while the reaction was cooled in ice. After fifteen minutes at 0° C., the ice bath was removed and the reaction was allowed to stir at room temperature for two hours. Aqueous NH4Cl (saturated) was added to quench the reaction and an aqueous workup was done extracting with ethyl acetate three times. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography (3% MeOH/DCM) to yield the title compound as a clear oil (818 mg, 100%).

Workup

  1. temperaturewas cooled in ice
  2. waitAfter fifteen minutes at 0° C.
  3. customthe ice bath was removed
  4. additionAqueous NH4Cl (saturated) was added
  5. customto quench
  6. customthe reaction
  7. extractionan aqueous workup was done extracting with ethyl acetate three times
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe crude product was purified by column chromatography (3% MeOH/DCM)

Sources & evidence

ORD record
ord-febd3f2e16214d13bb68a454c8b4ad42
Source dataset
uspto-grants-2010_08
Patent number
US07772235B2

Reaction notes

Loading…