Water → HCID 58883438, compound

HRID 2377527Notes

Reaction equation

HRID 2377527 reaction equation
[CH:1]([O:4][C:5](=[O:34])[C:6]1[CH:11]=[C:10]([C:12]#[C:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23]CCC[Si](C)(C)C)=[O:22])=[C:16]([F:31])[CH:15]=2)[CH:9]=[C:8]([C:32]#[CH:33])[CH:7]=1)([CH3:3])[CH3:2].O>CS(C)=O>[CH:1]([O:4][C:5](=[O:34])[C:6]1[CH:7]=[C:8]([C:32]#[CH:33])[CH:9]=[C:10]([C:12]#[C:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[C:16]([F:31])[CH:15]=2)[CH:11]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 962WaterHCID 86600203HCID 86600203, compound2×

Product 1

HCID 58883438HCID 58883438, compoundYield 38.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 3-ethynyl-5-[3-fluoro-4-(3-trimethylsilanyl-propoxycarbonylmethyl)-phenylethynyl]-benzoic acid isopropyl ester (Intermediate 207, 0.15 g, 0.32 mmol) in anhydrous dimethysulfoxide (4 mL) was treated with tetra-n-ethyl ammonium fluoride (0.19 mL, 1.3 mmol) and the resulting reaction mixture was stirred at ambient temperature for 5 min. Water was added and the reaction mixture was extracted with ethyl acetate. The organic phase was washed with water and brine, dried over anhydrous sodium sulfate, filtered and evaporated to an oil that was purified by recrystallization from ethyl acetate/hexane to afford the title compound as a white solid (0.045 g, 38%).

Workup

  1. customthe resulting reaction mixture
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated to an oil that
  7. customwas purified by recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-e1984222bb99412798fc8321bede8d47
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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