Hydrochloric Acid → 5-(6,6,6-Trifluorohexyl)thiophene-2-aldehyde

HRID 467146Notes

Reaction equation

HRID 467146 reaction equation
[F:1][C:2]([F:14])([F:13])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[S:9][CH:10]=[CH:11][CH:12]=1.C([Li])CCC.CN(C)[CH:22]=[O:23].Cl>O1CCCC1>[F:14][C:2]([F:1])([F:13])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[S:9][C:10]([CH:22]=[O:23])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 19813480HCID 19813480, compoundHCID 178418339Butyllithium

Product 1

HCID 198134935-(6,6,6-Trifluorohexyl)thiophene-2-aldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-25 °C

Procedure

To a solution of 2-(6,6,6-trifluorohexyl)thiophene (3.33 g) in dry tetrahydrofuran (30 ml) at -25° C. under nitrogen, was added n-butyllithium (8.2 ml, 2.5M) dropwise and the solution stirred at -25° C. for 2 hours. Dry dimethylformamide (2.34 ml) was then added dropwise and the solution stirred for a further hour, allowed to warm to room temperature and stirred for half hour. The reaction mixture was poured onto 2N hydrochloric acid (100 ml), extracted with ether (2×100 ml), dried over MgSO4 and evaporated under reduced pressure to give a brown oil. The oil was distilled under reduced pressure to give a yellow oil b.p. 114° C./1 mm.

Workup

  1. stirringthe solution stirred for a further hour
  2. temperatureto warm to room temperature
  3. stirringstirred for half hour
  4. extractionextracted with ether (2×100 ml)
  5. dry with materialdried over MgSO4
  6. customevaporated under reduced pressure
  7. customto give a brown oil
  8. distillationThe oil was distilled under reduced pressure

Sources & evidence

ORD record
ord-4afe318efe0640368b34c20d33753555
Source dataset
uspto-grants-1992_10
Patent number
US05158971

Reaction notes

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