Trifluoroacetic acid methylene chloride → Ether hydrochloride

HRID 1670265Notes

Reaction equation

HRID 1670265 reaction equation
[F:1][C:2]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1/[CH:11]=[CH:12]/[C:13]([O:15]C(C)(C)C)=[O:14].C(O)(C(F)(F)F)=O.C(Cl)[Cl:35]>>[ClH:35].[CH3:2][CH2:3][O:4][CH2:5][CH3:6].[F:1][C:2]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1/[CH:11]=[CH:12]/[C:13]([OH:15])=[O:14]

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 59852976HCID 59852976, compound

Product 2

HCID 10953452Ether hydrochlorideHCID 59853081HCID 59853081, compound

Procedure

(E)-tert-Butyl 3-(4-(2-fluoro-4-nitrophenoxy)pyridin-3-yl)acrylate (115 mg, 0.32 mmol) was treated with 1:1 TFA/CH2Cl2 (6 mL) and stirred at room temperature for 1.5 h. The mixture was concentrated under vacuum and the residue treated with MeOH (5 mL) and 2 M HCl/Et2O (15 mL) and concentrated under vacuum. A second treatment with MeOH (5 mL) and 2 M HCl/Et2O (15 mL) and reconcentration gave the title compound (120 mg). 1H NMR (DMSO-d6) δ 9.17 (s, 1H), 8.62 (d, 1H, J=6.6 Hz), 8.50 (dd, 1H, J=2.6, 10.1 Hz), 8.25 (d, 1H, J=9.1 Hz), 7.78 (d, 1H, J=16.3 Hz), 7.74 (dd, 1H, J=8.1, 8.6 Hz), 7.17 (d, 1H, J=6.1 Hz), 6.87 (d, 1H, J=16.3 Hz); MS (ESI+): m/z 305.11 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. additionthe residue treated with MeOH (5 mL) and 2 M HCl/Et2O (15 mL)
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-94f3707d5eae47c5a40d37c9115a48e3
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

Loading…