Water → HCID 14458175, compound

HRID 620240Notes

Reaction equation

HRID 620240 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]3[N:20]=[N:21][N:22]([CH2:24][CH2:25][CH2:26]Br)[N:23]=3)=[CH:14][CH:13]=2)=[C:6]([CH2:28][CH2:29][CH3:30])[C:5]=1[OH:31])(=[O:3])[CH3:2].[CH3:32][S:33]C.[Na].O.C(OCC)(=O)C>CS(C)=O>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]3[N:20]=[N:21][N:22]([CH2:24][CH2:25][CH2:26][S:33][CH3:32])[N:23]=3)=[CH:14][CH:13]=2)=[C:6]([CH2:28][CH2:29][CH3:30])[C:5]=1[OH:31])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14458166HCID 14458166, compoundHCID 86593196Sodium methylsulfide

Product 1

HCID 14458175HCID 14458175, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5-[(4-((4-Acetyl-3-hydroxy-2-propylphenyl)methoxy)phenyl)methyl]-2-(3-bromopropyl)-2H-tetrazole (3.1 g, 0.006 mol) was dissolved in DMSO (20 ml). A large excess of sodium methyl sulfide was added and the reaction mixture was stirred at room temperature for three hours. Water (100 ml) was added and the reaction mixture was extracted with ethyl acetate. The ethyl acetate layers were combined, washed with water and brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed by HPLC (preparatory-scale, silica gel column, eluted with a mixture of 9:1 toluene:ethyl acetate) to yield 2.1 g, 77.8% yield of the title product as a yellow oil which crystallized upon standing: n.m.r. (300 MHz, CDCl3) δ: 1.0 (t, 3H); 1.6 (m, 2H); 2.1 (s, 3H); 2.3 (m, 2H); 2.5 (m, 2H); 2.6 (s, 3H); 2.7 (t, 2H); 4.2 (s, 2 H); 4.7 (t, 2H); 5.1 (s, 1H); 6.9 (d, 2H); 7.0 (d, 1H); 7.3 (d, 2H); 7.6 (d, 1H); 12.7 (s, 1H).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed by HPLC (preparatory-scale, silica gel column
  7. washeluted with a mixture of 9:1 toluene

Sources & evidence

ORD record
ord-f544183d2dc94357b5d1fb42dbb75973
Source dataset
uspto-grants-1989_04
Patent number
US04820722

Reaction notes

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