Ethyl trifluoroacetate → HCID 59632690, compound

HRID 2369023Notes

Reaction equation

HRID 2369023 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[S:15][C:14]([C:16](=[O:18])[CH3:17])=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[F:29][C:30]([F:37])([F:36])[C:31](OCC)=[O:32]>C1COCC1>[F:29][C:30]([F:37])([F:36])[C:31](=[O:32])[CH2:17][C:16]([C:14]1[S:15][C:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=2)=[CH:12][CH:13]=1)=[O:18]

Participants

5

Reactant 3

HCID 9794Ethyl trifluoroacetateHCID 2733832Lithium HexamethyldisilazideHCID 59631757HCID 59631757, compound

Product 1

HCID 59632690HCID 59632690, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
1.5 °C

Procedure

Into a 250 mL flask was weighed 5.42 g (19.3 mmol) of 1-(5-(3-(methylsulfonyl)phenyl)thiophen-2-yl)ethanone and 42 mL of THF. The resulting suspension was stirred and cooled to 0-3° C. in an ice bath and 23 mL of a lithium bis(trimethylsilyl)amide solution (1.0 M in THF) was added. The resulting thick yellow suspension was stirred and allowed to warm to room temperature then ethyl trifluoroacetate (3.46 mL, 29 mmol) was added. After stirring at room temperature overnight the reaction was concentrated in vacuo to remove THF. The residue was washed into a separatory funnel with ethyl acetate and 1 M HCl. The ethyl acetate was separated, washed with brine, dried (MgSO4), and concentrated in vacuo. The resulting amorphous yellow powder was pure enough for further synthetic transformations, yield: 72 g (99%). 1H NMR (400 MHz, DMSO-d6): δ 8.20 (d, J=7 Hz, 1H), 8.08 (t, J=7 Hz, 1H), 7.95 (d, J=4.0 Hz, 1H), 7.89 (d, J=7 Hz, 1H), 7.78 (d, J=4 Hz, 1H), 7.69 (t, J=7 Hz, 1H), 6.22 (broad s, 1H), 3.26 (s, 3H).

Workup

  1. customInto a 250 mL flask was weighed
  2. stirringThe resulting thick yellow suspension was stirred
  3. temperatureto warm to room temperature
  4. stirringAfter stirring at room temperature overnight the reaction
  5. concentrationwas concentrated in vacuo
  6. customto remove THF
  7. washThe residue was washed into a separatory funnel with ethyl acetate and 1 M HCl
  8. customThe ethyl acetate was separated
  9. washwashed with brine
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-34238746f5d643dbaa5f0b591073c1ae
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

Loading…