Potassium tert-butoxide → HCID 67267855, compound

HRID 598163Notes

Reaction equation

HRID 598163 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH2:7]([N:14]1[C:23]2[C:18](=[C:19]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:25]=3[CH3:31])[CH:20]=[CH:21][CH:22]=2)[C:17](=[O:32])[C:16]([CH:33]=O)=[N:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CCOCC.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH2:7]([N:14]1[C:23]2[C:18](=[C:19]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:25]=3[CH3:31])[CH:20]=[CH:21][CH:22]=2)[C:17](=[O:32])[C:16]([CH:33]=[CH2:1])=[N:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 86613893HCID 86613893, compound

Product 1

HCID 67267855HCID 67267855, compoundYield 32%

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a slurry of 0.081 g (0.72 mmol) of potassium tert-butoxide in 10 mL of ether was added 0.22 g (0.60 mmol) of methyl triphenylphosphonium bromide. The resulting ylide solution was stirred for 30 min then 0.11 g (0.30 mmol) of 1-benzyl-5-(2,4-dimethylphenyl)-4-oxo-1,4-dihydrocinnoline-3-carbaldehyde was added. The reaction mixture was stirred for 3 h, diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, concentrated in vacuo and purified by flash chromatography eluting with a 9% ethyl acetate/hexanes mixture to give 0.035 g (32%) of the title compound as a light yellow solid.

Workup

  1. stirringThe reaction mixture was stirred for 3 h
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography
  8. washeluting with a 9% ethyl acetate/hexanes mixture

Sources & evidence

ORD record
ord-a3e2abf09c0a4092b75bc80092a82241
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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