2,2,2-Trifluoroethanol → HCID 18504973, compound

HRID 1760617Notes

Reaction equation

HRID 1760617 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([C:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH:11]=3)[S:7][C:6]=2[CH:16]=1.FC(F)(F)CO>[Pd].C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([CH:10]3[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]3)[S:7][C:6]=2[CH:16]=1

Participants

5

Reactant 2

HCID 64092,2,2-TrifluoroethanolHCID 21866114HCID 21866114, compound

Product 1

HCID 18504973HCID 18504973, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Scheme IA, Step C: To a solution of 4-(6-fluorobenzo[b]thiophen-2-yl)-1,2,5,6-tetrahydropyridine (0.850 g, 3.64 mmol) in a 3:1 mixture of ethanol (30 mL) and 2,2,2-trifluoroethanol (10 mL) was added 10% Pd/C (0.900 g). The black slurry was stirred vigorously at room temperature under hydrogen (balloon pressure) for 1 day. The black slurry was then filtered over a pad of diatomaceous earth and washed with ethanol. The filtrate was concentrated to provide the intermediate title compound as a white solid (0.735 g, 86%). mp 115-120° C. IR (KBr) 3350 (br), 1247 cm1. Ion Spray MS 236 (M+H)+.

Workup

  1. filtrationThe black slurry was then filtered over a pad of diatomaceous earth
  2. washwashed with ethanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-3c7c8bde1dc74404a973801f51be623f
Source dataset
uspto-grants-2005_01
Patent number
US06844344B2

Reaction notes

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