Hydrofluoric Acid → HCID 53844584, compound

HRID 2225839Notes

Reaction equation

HRID 2225839 reaction equation
[CH3:1][O:2][C:3](=[O:35])[C:4](=[O:34])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][CH:15]([O:26][Si](C(C)(C)C)(C)C)[C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=2)=[CH:7][CH:6]=1.F.C(=O)(O)[O-].[Na+]>C(#N)C>[CH3:1][O:2][C:3](=[O:35])[C:4](=[O:34])[C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][CH2:13][CH2:14][CH:15]([OH:26])[C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 14917Hydrofluoric AcidHCID 516892Sodium BicarbonateHCID 54203999HCID 54203999, compound

Product 1

HCID 53844584HCID 53844584, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of rac-4-[4-[[(1,1 -dimethylethyl)dimethylsilyl]oxy]-4-(2-naphthalenyl) butoxy]-alpha-oxobenzeneacetic acid methyl ester (1.0 g) in acetonitrile (22.5 mL) containing 48% aqueous hydrofluoric acid solution (2.5 mL) was stirred at room temperature for 1 hour. The reaction mixture was poured into saturated sodium bicarbonate solution and extracted with ethyl acetate (3×10 mL). The combined organic extracts were dried (MgSO4) and evaporated to provide 0.76 g of crude product that was purified by flash chromatography over silica gel (ethyl acetate-hexane; 7:13) to yield 0.554 g of rac-4-[4-hydroxy-4-(2-naphthalenyl)butoxy]-alpha-oxobenzeneacetic acid methyl ester as an oil.

Workup

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. customevaporated
  4. customto provide 0.76 g of crude product that
  5. customwas purified by flash chromatography over silica gel (ethyl acetate-hexane; 7:13)

Sources & evidence

ORD record
ord-4e8e84c62fe941279b9762aac405df03
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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