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

HRID 1099155Notes

Reaction equation

HRID 1099155 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.CCCCCC>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

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8058HexaneHCID 12052TriethylsilaneHCID 57911478(Z)-1-(2,3-difluorophenyl)cyclohept-4-enol

Product 1

HCID 579114735-(2,3-Difluorophenyl)cyclohept-1-eneYield 88.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 250 mL round-bottomed flask (t=g) was added (Z)-1-(2,3-difluorophenyl)cyclohept-4-enol (2.05 g, 9.14 mmol) in CH2Cl2 (40 mL) to give a colorless solution. Triethylsilane (7.30 mL, 45.7 mmol) was added, followed by TFA (20 mL). The mixture was stirred at room temperature for 3 hours: TLC showed a complete conversion (Rf=0.42 by pure hexane). It was concentrated down to a bi-layer oil (the lower layer wasn't hexane-soluble). Purification by FCC using only hexane afforded the desired product as a colorless oil (1.684 g, 88%). 1H NMR (400 MHz, CDCl3) δ 7.00-6.90 (m, 3H), 5.90-5.82 (m, 2H), 3.20-3.05 (m, 1H), 2.40-2.15 (m, 4H), 1.90-1.78 (m, 2H), 1.60-1.40 (m, 2H).

Workup

  1. customto give a colorless solution
  2. concentrationIt was concentrated down to a bi-layer oil (the lower layer wasn't hexane-soluble)
  3. customPurification by FCC

Sources & evidence

ORD record
ord-fb26ed9fbdc444df80247c91dc741fce
Source dataset
uspto-grants-2012_03
Patent number
US08143403B2

Reaction notes

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