Sulfuric Acid → HCID 22729011, compound

HRID 2085172Notes

Reaction equation

HRID 2085172 reaction equation
[CH3:1][C:2](=[N:4][OH:5])[CH3:3].C([Li])CCC.[CH3:11][O:12][C:13]1[C:21]2[CH:20]=[C:19]([C:22](OC)=O)[O:18][C:17]=2[CH:16]=[CH:15][CH:14]=1.S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>C1COCC1>[CH3:11][O:12][C:13]1[C:21]2[CH:20]=[C:19]([C:22]3[O:5][N:4]=[C:2]([CH3:3])[CH:1]=3)[O:18][C:17]=2[CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 67180Acetone, oximeHCID 516892Sodium BicarbonateHCID 22729192HCID 22729192, compoundHCID 178418339Butyllithium

Product 1

HCID 22729011HCID 22729011, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution (160 ml) of acetone oxime (5.0 g) in THF was added dropwise n-butyllithium (1.6 M hexane solution) over 15 min under ice-cooling and the mixture was stirred for 1 hr. Thereto was added dropwise a solution (60 ml) of methyl 4-methoxybenzo(b)furan-2-carboxylate (6.7 g) in THF and the mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into ice water, and conc. sulfuric acid (4 ml) was added carefully. The mixture was stirred for 20 min more. The aqueous layer was neutralized with sodium hydrogencarbonate and extracted with ethyl acetate. After washing with water, the organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure to give the title compound (3.0 g) as yellow crystals.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 2 hr
  3. additionwas added carefully
  4. stirringThe mixture was stirred for 20 min more
  5. extractionextracted with ethyl acetate
  6. washAfter washing with water
  7. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-89fbf8ae90f54bac8472ead640f59394
Source dataset
uspto-grants-2004_04
Patent number
US06720320B2

Reaction notes

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