Trifluoroacetic acid → HCID 11962811, compound

HRID 1715221Notes

Reaction equation

HRID 1715221 reaction equation
O[C:2]1([C:16]2[C:24]([OH:25])=[CH:23][C:19]3[O:20][CH2:21][O:22][C:18]=3[CH:17]=2)[C:6](=[O:7])[N:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:4]2[CH:13]=[CH:14][S:15][C:3]1=2.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(Cl)Cl>[OH:25][C:24]1[C:16]([CH:2]2[C:6](=[O:7])[N:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:4]3[CH:13]=[CH:14][S:15][C:3]2=3)=[CH:17][C:18]2[O:22][CH2:21][O:20][C:19]=2[CH:23]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 11962773HCID 11962773, compound

Product 1

HCID 11962811HCID 11962811, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6-hydroxy-6-(6-hydroxy-1,3-benzodioxol-5-yl)-4-pentyl-4,6-dihydro-5H-thieno[3,2-b]pyrrol-5-one (1.71 g, 4.70 mmol) in CH2Cl2 (30.0 mL) were added trifluoroacetic acid (6.00 g, 52.6 mmol) and triethylsilane (5.00 g, 43.0 mmol) at 0° C. The reaction mixture was stirred at ambient temperature for 16 hours and diluted with CH2Cl2 (50.0 mL). The mixture was washed with water (2×50.0 mL), dried over Na2SO4 and filtered. The filtrate was evaporated under reduced pressure. The residue was subjected to column chromatography to give the title compound (0.80 g, 49%) as a green solid: MS (ES+) m/z 346.4 (M+1).

Workup

  1. washThe mixture was washed with water (2×50.0 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-33036f4207504f578432a0e393a5e87b
Source dataset
uspto-grants-2010_09
Patent number
US07799798B2

Reaction notes

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