1,4-Dimethoxybutan-2-one → HCID 21094561, compound

HRID 1350539Notes

Reaction equation

HRID 1350539 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:13](=[CH:14][N:15]([CH3:18])[N:16]=3)[CH:12]=[CH:11][CH:10]=2)=[C:5]([CH3:19])[CH:4]=1.[Li]CCCC.[CH3:25][O:26][CH2:27][C:28](=[O:33])[CH2:29][CH2:30][O:31][CH3:32]>C1COCC1.CCOC(C)=O>[CH3:25][O:26][CH2:27][C:28]([C:14]1[N:15]([CH3:18])[N:16]=[C:17]2[C:13]=1[CH:12]=[CH:11][CH:10]=[C:9]2[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH3:19])([OH:33])[CH2:29][CH2:30][O:31][CH3:32]

Participants

6

Reactant 3

HCID 2669141,4-Dimethoxybutan-2-oneHCID 210946097-(4-Methoxy-2-methyl-phenyl)-2-methyl-2H-indazoleHCID 178418339Butyllithium

Product 1

HCID 21094561HCID 21094561, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

Indazole 4c (0.29 g, 0.79 mMol) was dissolved in 5 mL dry THF under a nitrogen atmosphere and cooled to −78° C. n-BuLi (0.4 mL of 2.5 M hexane solution, 1 mMol) was added dropwise via syringe, and stirred at −78° C. for 10 minutes. 1,4-dimethoxy-2-butanone (0.16 g, 1.18 mMol) was added dropwise at −78° C. and then the reaction mixture was allowed to warm to rt. The reaction mixture was diluted with EtOAc (50 mL) and washed successively with saturated ammonium chloride solution, brine and dried over magnesium sulfate. Evaporation of the solvent afforded crude material which was flash chromatographed on silica and eluted with hexane:EtOAc (3:1) which afforded 27c as an oil (0.196 g; 65%).

Workup

  1. additionwas added dropwise via syringe
  2. temperatureto warm to rt
  3. washwashed successively with saturated ammonium chloride solution, brine
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent
  6. customafforded crude material which
  7. customchromatographed on silica
  8. washeluted with hexane:EtOAc (3:1) which

Sources & evidence

ORD record
ord-ff809157bae8413b971bc99d7eb0a199
Source dataset
uspto-grants-2007_05
Patent number
US07214699B2

Reaction notes

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