Trifluoroacetic acid → HCID 19047187, compound

HRID 1780595Notes

Reaction equation

HRID 1780595 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([S:7][CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[S:5][CH:6]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][C:2]1[C:3]2[C:10]([CH3:12])([CH3:11])[CH2:9][CH2:8][S:7][C:4]=2[S:5][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 190471884-Methyl-2-[(3-methylbut-2-en-1-yl)sulfanyl]thiophene

Product 1

HCID 19047187HCID 19047187, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 17.36 g (0.088 mol) of the title compound of Step A in 300 mL of methylene chloride was added dropwise to 300 mL of trifluoroacetic acid under nitrogen. After stirring at room temperature overnight, the mixture was evaporated to dryness. The residue was dissolved in 500 mL of methylene chloride, washed with 5% sodium bicarbonate (2×500 mL), dried (MgSO4), filtered, and evaporated to dryness. The crude product was chromatographed on silica gel eluting with hexane to yield 8.26 g of the title compound of Step B as an oil. 1H NMR (CDCl3): δ 1.32 (s,6H), 2.0 (m,2H), 2.3 (s,3H), 3.0 (m,2H), 6.6 (s, 1H).

Workup

  1. customthe mixture was evaporated to dryness
  2. dissolutionThe residue was dissolved in 500 mL of methylene chloride
  3. washwashed with 5% sodium bicarbonate (2×500 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe crude product was chromatographed on silica gel eluting with hexane

Sources & evidence

ORD record
ord-06dfd4c47a1244c6a03cdd0e38eeceb9
Source dataset
uspto-grants-1997_05
Patent number
US05631210

Reaction notes

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