Diethyl Ether → 2-{3-[3-(2-Ethyl-5-hydroxy-4-oxazol-4-yl-phenoxy)propoxy]-2-propyl-phenoxy}benzoic acid

HRID 1008299Notes

Reaction equation

HRID 1008299 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[N:37]=[CH:38][O:39][CH: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.CCOCC>C(S)C>[CH2:41]([C:23]1[CH:24]=[C:25]([C:36]2[N:37]=[CH:38][O:39][CH: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 3

HCID 3283Diethyl EtherHCID 8000Boron trifluoride etherateHCID 601111942-{3-[3-(5-Benzyloxy-2-ethyl-4-oxazol-4-yl-phenoxy)propoxy]-2-propylphenoxy}benzoic acid methyl ester

Product 1

HCID 98066212-{3-[3-(2-Ethyl-5-hydroxy-4-oxazol-4-yl-phenoxy)propoxy]-2-propyl-phenoxy}benzoic acidYield 46.9%

Reagents, catalysts & solvents 1

HCID 6343EthanethiolSolvent

Procedure

To a solution of 2-{3-[3-(5-benzyloxy-2-ethyl-4-oxazol-4-yl-phenoxy)propoxy]-2-propylphenoxy}benzoic acid methyl ester (89 mg, 0.14 mmol) in ethanethiol (2 mL) was treated with boron trifluoride etherate (0.27 mL, 2.2 mmol) at room temperature for 4 h. The solution was poured into ether and washed once with water, once with saturated sodium bicarbonate solution, once with saturated sodium chloride solution, dried (sodium sulfate), filtered, and concentrated in vacuo. Chromatography (silica gel, 15% ethyl acetate/85% hexane) of the residue provided 34 mg (45%) of the title product as a light brown oil. 1H NMR (CDCl3) δ 7.99 (d, J=1 Hz, 1H), 7.90 (d, J=1 Hz, 1H), 7.88 (dd, J=8, 2 Hz, 1H), 7.38 (t, J=7 Hz, 1H), 7.15 (s, 1H), 7.10 (d, J=9 Hz, 1H), 7.06 (d, J=9 Hz, 1H), 6.81 (d, J=9 Hz, 1H), 6.70 (d, J=9 Hz, 1H), 6.52 (s, 1H), 6.44 (d, J=9 Hz, 1H), 4.20 (m, 4H), 3.83 (s, 3H), 2.65 (t, J=8 Hz, 2H), 2.58 (q, J=8 Hz, 2H), 2.33 (quintet, J=6 Hz, 2H), 1.55 (hextet, J=7 Hz, 2H), 1.17 (t, J=8 Hz, 3H), 0.91 (t, J=8 Hz, 3H); MS ES+m/e=532 (p+1).

Workup

  1. washwashed once with water, once with saturated sodium bicarbonate solution, once with saturated sodium chloride solution
  2. dry with materialdried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a514142ccb294132881baf5b847ab50b
Source dataset
uspto-grants-2004_09
Patent number
US06797723B1

Reaction notes

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