Trifluoroacetic acid → 5-(2,3-Difluorophenyl)cyclohept-1-ene

HRID 1099149Notes

Reaction equation

HRID 1099149 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1(O)[CH2:15][CH2:14][CH:13]=[CH:12][CH2:11][CH2:10]1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:15][CH2:14][CH:13]=[CH:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 57911478(Z)-1-(2,3-difluorophenyl)cyclohept-4-enol

Product 1

HCID 579114735-(2,3-Difluorophenyl)cyclohept-1-eneYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 100 mL round-bottomed flask (t=g) was added (Z)-1-(2,3-difluorophenyl)cyclohept-4-enol (872 mg, 3.89 mmol) in CH2Cl2 (16 mL) to give a colorless solution. Triethylsilane (3.11 mL, 19.44 mmol) was added, following by TFA (8.00 mL). The mixture was stirred at room temperature for 2.5 hours. TLC showed clean conversion to a less polar compound. It was concentrated down and purification by FCC up to 20% Et2O in hexane afforded the desired product as a colorless oil (769 mg, 95%). The product was quickly eluted out. 1H NMR (the major peaks are the same as these in the later synthesis) confirmed the structure.

Workup

  1. customto give a colorless solution
  2. concentrationIt was concentrated down and
  3. custompurification by FCC up to 20% Et2O in hexane

Sources & evidence

ORD record
ord-f39fdd9682454939a8e009bf028bfac0
Source dataset
uspto-grants-2012_03
Patent number
US08143403B2

Reaction notes

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