Boron trifluoride etherate → 2-(3-{3-[2-Ethyl-5-hydroxy-4-(2H-pyrazol-3-yl)phenoxy]propoxy}-2-propyl-phenoxy)benzoic acid

HRID 1008307Notes

Reaction equation

HRID 1008307 reaction equation
C([O:8][C:9]1[C:10]([C:41]2[NH:42][N:43]=[CH:44][CH:45]=2)=[CH:11][C:12]([CH2:39][CH3:40])=[C:13]([CH:38]=1)[O:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[C:20]([CH2:35][CH2:36][CH3:37])=[C:21]([CH:32]=[CH:33][CH:34]=1)[O:22][C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25]([OH:27])=[O:26])C1C=CC=CC=1.B(F)(F)F.CCOCC>C(S)C.C(OCC)C.O>[CH2:39]([C:12]1[CH:11]=[C:10]([C:41]2[NH:42][N:43]=[CH:44][CH:45]=2)[C:9]([OH:8])=[CH:38][C:13]=1[O:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[C:20]([CH2:35][CH2:36][CH3:37])=[C:21]([CH:32]=[CH:33][CH:34]=1)[O:22][C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25]([OH:27])=[O:26])[CH3:40]

Participants

6

Reactant 2

HCID 8000Boron trifluoride etherate2×HCID 226662492-(3-{3-[5-benzyloxy-2-ethyl-4-(2H-pyrazol-3-yl)phenoxy]propoxy}-2-propylphenoxy)benzoic acid

Product 1

HCID 1355289882-(3-{3-[2-Ethyl-5-hydroxy-4-(2H-pyrazol-3-yl)phenoxy]propoxy}-2-propyl-phenoxy)benzoic acidYield 24%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6343EthanethiolSolvent

Procedure

A solution of 2-(3-{3-[5-benzyloxy-2-ethyl-4-(2H-pyrazol-3-yl)phenoxy]propoxy}-2-propylphenoxy)benzoic acid (300 mg, 0.490 mmol) in ethanethiol (2.5 mL) was treated with boron trifluoride etherate (2 mL) at room temperature for 3 h, at which time an additional portion of boron trifluoride etherate (1 mL) was added and stirring resumed for an additional 1 h. The mixture was diluted with diethyl ether and water. The organic layer was separated, washed with water, dried (sodium sulfate), filtered, and concentrated in vacuo. Chromatography (silica gel, 15% ethyl acetate/85% hexane to 60% ethyl acetate/40% hexane) of the residue provided 60 mg (24%) of the title compound as a white solid. 1H NM (CDCl3) δ 8.23 (d, J=8Hz, 1H), 7.61 (s, 1H), 7.42 (t, J=7 Hz, 1H), 7.30 (s, 1H), 7.19 (d, J=8 Hz, 1H), 7.15 (d, J=8 Hz, 1H), 6.81 (d, J=8 Hz, 1H), 6.69 (d, J=8 Hz, 1H), 6.61 (s, 1H), 6.60 (d, J=8 Hz, 1H), 6.54 (s, 1H), 4.20 (m, 4H), 2.58 (m, 4H), 2.33 (quintet, J=6 Hz, 2H), 1.48 (hextet, J=8 Hz, 2H), 1.17 (t, J=8 Hz, 3H), 0.86 (t, J=7 Hz, 3H); TOF MS ES+ exact mass calculated for C30H33N2O6 (p+1): m/z=517.2339. Found: 517.2334. IR (CHCl3, cm−1) 2965, 1738, 1454. Anal. Calcd for C30H32N2O6: C, 69.75; H, 6.24; N, 5.42. Found: C, 69.73; H, 6.33; N, 5.25.

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fe7c679ceb424ee186d9faed1cbd2dee
Source dataset
uspto-grants-2004_09
Patent number
US06797723B1

Reaction notes

Loading…