Diethyl Ether → HCID 18511418, compound

HRID 1370329Notes

Reaction equation

HRID 1370329 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:12]=[C:11]([CH:13]2[CH2:15][O:14]2)[C:10]2[C:5](=[C:6]([C:16]([F:19])([F:18])[F:17])[CH:7]=[CH:8][CH:9]=2)[N:4]=1.B(F)(F)F.C([O-])(O)=[O:27].[Na+].[CH3:31][CH2:32]OCC>>[F:1][C:2]([F:21])([F:20])[C:3]1[CH:12]=[C:11]([CH:13]([CH2:15][O:14][CH2:31][CH3:32])[OH:27])[C:10]2[C:5](=[C:6]([C:16]([F:17])([F:18])[F:19])[CH:7]=[CH:8][CH:9]=2)[N:4]=1

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 6356Boron trifluorideHCID 516892Sodium BicarbonateHCID 122545662-[2,8-Bis(trifluoromethyl)-4-quinolyl]oxirane

Product 1

HCID 18511418HCID 18511418, compoundYield 82%

Procedure

A solution of (2,8-bis(trifluoromethyl)-4-quinolinyl)oxirane (208 mg, 0.68 mmol) in ether (3 mL) was treated with BF3.etherate (0.2 mL), stirred at room temperature for 2 h, poured into dilute NaHCO3 (20 mL) and extracted with EtOAc (2×20 mL). The combined extracts were dried (MgSO4), concentrated in vacuo and the residue purified by flash chromatography [SiO2; heptane-EtOAc (2:1)] to give the title compound (196 mg, 82%) as a yellow oil: IR νmax (Nujol)/cm−1 3700-3200, 3087, 2982, 2879, 1606, 1586, 1431, 1372, 1311, 1191, 1144, 1109, 769; NMR δH (400 MHz, CDCl3) 1.26 (3H, t, J 7.0 Hz), 3.24-3.31 (1H, br s), 3.48 (1H, dd, J 8.4, 9.6 Hz), 3.54-3.69 (2H, m), 3.84 (1H, dd, J 9.6, 3.2 Hz), 5.70 (1H, dd, J 8.4, 3.2 Hz), 7.75 (1H, t, J 7.9 Hz), 8.13 (1H, s), 8.17 (1H, d, J 7.5 Hz), 8.28 (1H, d, J 9.1 Hz); M/Z 354 (M+H)+.

Workup

  1. extractionextracted with EtOAc (2×20 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customthe residue purified by flash chromatography [SiO2; heptane-EtOAc (2:1)]

Sources & evidence

ORD record
ord-0461b5d1416d441eb235f4c2425abf08
Source dataset
uspto-grants-2003_06
Patent number
US06583156B1

Reaction notes

Loading…