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

HRID 1008309Notes

Reaction equation

HRID 1008309 reaction equation
C[O:2][C:3](=[O:46])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([O:28]CC3C=CC=CC=3)[C:25]([C:36]3[S:37][CH:38]=[CH:39][N:40]=3)=[CH:24][C:23]=2[CH2:41][CH3:42])[C:12]=1[CH2:43][CH2:44][CH3:45].B(F)(F)F.CCOCC>C(S)C.O>[CH2:41]([C:23]1[CH:24]=[C:25]([C:36]2[S:37][CH:38]=[CH:39][N:40]=2)[C:26]([OH:28])=[CH:27][C:22]=1[O:21][CH2:20][CH2:19][CH2:18][O:17][C:13]1[C:12]([CH2:43][CH2:44][CH3:45])=[C:11]([CH:16]=[CH:15][CH:14]=1)[O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]([OH:46])=[O:2])[CH3:42]

Participants

5

Reactant 2

HCID 8000Boron trifluoride etherateHCID 601163722-{3-[3-(5-Benzyloxy-2-ethyl-4-thiazol-2-yl-phenoxy)propoxy]-2-propylphenoxy}benzoic acid methyl ester

Product 1

HCID 1355369512-{3-[3-(2-Ethyl-5-hydroxy-4-thiazol-2-yl-phenoxy)propoxy]-2-propyl-phenoxy}benzoic acidYield 45.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6343EthanethiolSolvent

Procedure

A solution of 2-{3-[3-(5-benzyloxy-2-ethyl-4-thiazol-2-yl-phenoxy)propoxy]-2-propylphenoxy}benzoic acid methyl ester (282 mg, 0.442 mmol) in ethanethiol (3 mL) was treated with boron trifluoride etherate (0.56 mL, 4.4 mmol) at room temperature for 3 h. The reaction mixture was diluted with water, concentrated in vacuo, and extracted with diethyl ether. The organic layer was dried (magnesium sulfate), filtered, and concentrated in vacuo. Chromatography (silica gel, ethyl acetate/hexane) provided 107 mg (44%) of the title compound. 1H NMR (CDCl3) δ 7.88 (dd, J=8, 2 Hz, 1H), 7.80 (d, J=4 Hz, 1H), 7.35 (dt, J=8, 2 Hz, 1H), 7.28 (d, J=4 Hz, 1H), 7.24 (s, 1H), 7.09 (dt, J=9, 2 Hz, 1H), 7.05 (t, J=9 Hz, 1H), 6.79 (d, J=9 Hz, 1H), 6.66 (d, J=9 Hz, 1H), 6.61 (s, 1H), 6.42 (d, J=9 Hz, 1H), 4.24 (t, J=6 Hz, 2H), 4.18 (t, J=6 Hz, 2H), 3.81 (s, 3H), 2.63 (t, J=7 Hz, 2H), 2.58 (q, J=7 Hz, 2H), 2.34 (quintet, J=6 Hz, 2H), 1.52 (hextet, J=8 Hz, 2H), 1.17 (t, J=7 Hz, 3H), 0.88 (t, J=7 Hz, 3H); MS ES+ m/e 548 (p+1).

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with diethyl ether
  3. dry with materialThe organic layer was dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-452d4c2204dc4efa8c71dcebf6fc3d22
Source dataset
uspto-grants-2004_09
Patent number
US06797723B1

Reaction notes

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