Sulfuric Acid → HCID 15838028, compound

HRID 1599505Notes

Reaction equation

HRID 1599505 reaction equation
[C:1]([O:4][CH:5]([CH2:18][O:19]C1CCCCO1)[C:6]#[C:7][C:8]1[S:12][C:11]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[CH:10][CH:9]=1)(=[O:3])[CH3:2].OS(O)(=O)=O>CO>[C:1]([O:4][CH:5]([CH2:18][OH:19])[C:6]#[C:7][C:8]1[S:12][C:11]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[CH:10][CH:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 18920418HCID 18920418, compound

Product 1

HCID 15838028HCID 15838028, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(3-Acetoxy-4-tetrahydropyranyloxy-1-butynyl)-2,2'-bithiophene (2.8 g) was dissolved in methanol (40 ml). H2SO4 solution (3 ml, 2N) was added slowly in ice bath and stirred at room temperature for 2 hours. The reaction solution was extracted with ethyl acetate. The extract was thus washed with 10 ml of NaHCO3 three time, 50 ml of water twice and dried over anhydrous magnesium sulfate. After removal of solvent residual solid was purified by silica gel column chromatography, eluted with ethyl acetate/n-hexane (1/3). Light brown product (1.83 g, 84%) was obtained.

Workup

  1. extractionThe reaction solution was extracted with ethyl acetate
  2. washThe extract was thus washed with 10 ml of NaHCO3 three time, 50 ml of water twice
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removal of solvent residual solid
  5. customwas purified by silica gel column chromatography
  6. washeluted with ethyl acetate/n-hexane (1/3)

Sources & evidence

ORD record
ord-95a686680e5c42a895a80f092ead6dd8
Source dataset
uspto-grants-1998_04
Patent number
US05741811

Reaction notes

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