Sodium Methoxide → HCID 11303923, compound

HRID 2358294Notes

Reaction equation

HRID 2358294 reaction equation
[C:1]([C:9]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:10]=1[C:11]([N:13]([CH2:22][C:23]#[N:24])[CH2:14][CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])=[O:12])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+]>CO>[C:23]([C:22]1[N:13]([CH2:14][CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])[C:11](=[O:12])[C:10]2[C:9]([C:1]=1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[CH:28][C:27]([O:29][CH3:30])=[CH:26][CH:25]=2)#[N:24]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 58828525HCID 58828525, compound

Product 1

HCID 11303923HCID 11303923, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5 (1.05 g, 2.65 mmol), sodium methoxide (4.62M in methanol, 1.43 mL, 6.63 mmol) and methanol (50 mL) was heated at reflux for 2 h. The solvent was removed in vacuo and sat. sodium bicarbonate was added. The resulting mixture was extracted with methylene chloride (3×). The combined organic extracts were dried with magnesium sulfate (anh.) and filtered. The filtrate was concentrated in vacuo to give an oil which was triturated with hexane/ethyl acetate to give 6 as a white solid (805 mg, 77%)

Workup

  1. temperatureat reflux for 2 h
  2. customThe solvent was removed in vacuo and sat. sodium bicarbonate
  3. additionwas added
  4. extractionThe resulting mixture was extracted with methylene chloride (3×)
  5. dry with materialThe combined organic extracts were dried with magnesium sulfate (anh.)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo
  8. customto give an oil which
  9. customwas triturated with hexane/ethyl acetate

Sources & evidence

ORD record
ord-7b9d7ce83d094a569b6d46a361fd433c
Source dataset
uspto-grants-2010_07
Patent number
US07763614B2

Reaction notes

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