Trifluoroacetic acid → HCID 68183051, compound

HRID 1615484Notes

Reaction equation

HRID 1615484 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[C:13]3[CH:14]=[C:15]([C:17]4[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=4)[S:16][C:12]=3[CH2:11][CH2:10][C:9]2([CH3:24])[CH3:23])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13]3[CH:14]=[C:15]([C:17]4[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=4)[S:16][C:12]=3[CH2:11][CH2:10][C:9]2([CH3:24])[CH3:23])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 68183080HCID 68183080, compound

Product 1

HCID 68183051HCID 68183051, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
90 °C

Procedure

4-(4-chlorophenyl)-5,5-dimethyl-2-pyridin-4-yl-4,5,6,7-tetrahydro-1-benzothiophene-4-ol (240 mg, 0.65 mmol) was placed in a 100 mL round bottomed flask and dissolved in 1,2-dichloroethane (10 mL). To the solution were added trifluoroacetic acid (1 mL, 10 mmol) and triethylsilane (1 mL, 6 mmol). The resulting yellow solution was stirred for 16 hr at 90° C. The mixture was allowed to cool to rt and then concentrated under reduced pressure. The residue was diluted with EtOAc (50 mL) and the resulting solution was washed with a saturated aqueous solution of NaHCO3 (50 mL). The aqueous phase was separated and extracted with EtOAc (50 mL). The combined organic phases were dried over anhydrous MgSO4. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by pre-packed silica gel (24 g) column chromatography, eluting with a 30% to 100% EtOAc in hexane to obtain product as colorless syrup. LCMS: (FA) ES+354, 356; 1H NMR (400 MHz, d-chloroform) δ ppm 8.49 (dd, 2H), 7.31 (dd, 2H), 7.20 (d, 2H), 7.03 (d, 2H), 6.84 (s, 1H), 3.67 (s, 1H), 2.83-3.00 (m, 2H), 1.77-1.82 (m, 1H), 1.63-1.70 (m, 1H), 1.04 (s, 3H), 0.74 (s, 3H).

Workup

  1. temperatureto cool to rt
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with EtOAc (50 mL)
  4. washthe resulting solution was washed with a saturated aqueous solution of NaHCO3 (50 mL)
  5. customThe aqueous phase was separated
  6. extractionextracted with EtOAc (50 mL)
  7. dry with materialThe combined organic phases were dried over anhydrous MgSO4
  8. customInsoluble materials were removed by filtration
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe residue was purified by pre-packed silica gel (24 g) column chromatography
  11. washeluting with a 30% to 100% EtOAc in hexane
  12. customto obtain product as colorless syrup

Sources & evidence

ORD record
ord-6d7a637bcf914fe287c1d4ff5a0971fb
Source dataset
uspto-grants-2014_07
Patent number
US08765746B2

Reaction notes

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