Water → HCID 86644309, compound

HRID 1191561Notes

Reaction equation

HRID 1191561 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]#[C:16][Si](C)(C)C)=[CH:11][CH:10]=2)=[CH:5][C:4]=1[CH:21]1[C:26](=[O:27])[C:25]([CH3:29])([CH3:28])[O:24][C:23]([CH3:31])([CH3:30])[C:22]1=[O:32])[CH3:2].C(=O)([O-])[O-].[K+].[K+].O>CO>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]([C:15]#[CH:16])=[CH:13][CH:14]=2)=[CH:5][C:4]=1[CH:21]1[C:22](=[O:32])[C:23]([CH3:31])([CH3:30])[O:24][C:25]([CH3:29])([CH3:28])[C:26]1=[O:27])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 68481571HCID 68481571, compound

Product 1

HCID 86644309HCID 86644309, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-[4-ethyl-4′-(trimethylsilylethynyl)biphenyl-3-yl]-2,2,6,6-tetramethyl-pyran-3,5-dione (0.143 g, 0.32 mmol) in methanol (6.5 ml) is added powdered potassium carbonate (0.177 g, 1.28 mmol), and the mixture is stirred at room temperature for 1 hour. Water is then added to dissolve all inorganics, and the mixture is concentrated in vacuo. 2M hydrochloric acid is added to achieve pH 2-3, then the desired material is extracted with ethyl acetate (×3). All organics are combined, washed with brine, dried over anhydrous magnesium sulfate then concentrated in vacuo. The residue is further purified by flash column chromatography on silica gel (hexane/ethyl acetate 4:1 ratio) to afford 4-(4-ethyl-4′-ethynylbiphenyl-3-yl)-2,2,6,6-tetramethylpyran-3,5-dione (0.070 g) as a yellow solid.

Workup

  1. dissolutionto dissolve all inorganics
  2. concentrationthe mixture is concentrated in vacuo
  3. addition2M hydrochloric acid is added
  4. extractionthe desired material is extracted with ethyl acetate (×3)
  5. washwashed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationthen concentrated in vacuo
  8. customThe residue is further purified by flash column chromatography on silica gel (hexane/ethyl acetate 4:1 ratio)

Sources & evidence

ORD record
ord-b5ce6a98929d4907ba3df6babea4d9f3
Source dataset
uspto-grants-2014_03
Patent number
US08680012B2

Reaction notes

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