Trifluoroacetic acid → HCID 68183051, compound

HRID 1615531Notes

Reaction equation

HRID 1615531 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, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
90 °C

Procedure

In a 100 mL round bottomed flask was placed 4-(4-chlorophenyl)-5,5-dimethyl-2-pyridin-4-yl-4,5,6,7-tetrahydro-1-benzothiophene-4-ol (240 mg, 0.65 mmol) and 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 then was concentrated under reduced pressure. The residue was diluted with EtOAc, then was washed with a saturated aqueous solution of NaHCO3 (50 mL). The aqueous phase was 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 using column chromatography on silica gel (24 g RediSep column, gradient 30% EA in hexane to 100% EA in hexane) to give the product (215 mg, 94%) as a colorless syrup: 1H NMR (400 MHz, CDCl3) δ: 8.49 (dd, 2H), 7.31 (dd, 2H), 7.25-7.27 (m, 2H), 7.03 (br d, 2H), 6.84 (s, 1H), 3.67 (s, 1H), 1.77-1.83 (m, 1H), 1.63-1.70 (m, 1H), 1.03 (s, 3H), 0.74 (s, 3H).

Workup

  1. customIn a 100 mL round bottomed flask was placed
  2. temperatureto cool to rt
  3. concentrationthen was concentrated under reduced pressure
  4. additionThe residue was diluted with EtOAc
  5. washwas washed with a saturated aqueous solution of NaHCO3 (50 mL)
  6. extractionThe aqueous phase was extracted 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

Sources & evidence

ORD record
ord-04ac493ce1034fac93177ce5f6b2383c
Source dataset
uspto-grants-2014_07
Patent number
US08765746B2

Reaction notes

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