Methyl Ethyl Ketone → 5-[(4-((4-Acetyl-3-hydroxy-2-propylphenyl)methoxy)phenyl)]-2-(3-bromopropyl)-2H-tetrazole

HRID 620241Notes

Reaction equation

HRID 620241 reaction equation
[Na].[OH:2][C:3]1[C:8]([CH2:9][CH2:10][CH3:11])=[C:7]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[NH:24][N:23]=[N:22][N:21]=3)=[CH:16][CH:15]=2)[CH:6]=[CH:5][C:4]=1[C:25](=[O:27])[CH3:26].[Br:28][CH2:29][CH2:30][CH2:31]Br.CCC(C)=O.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[C:25]([C:4]1[CH:5]=[CH:6][C:7]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[N:21]=[N:22][N:23]([CH2:31][CH2:30][CH2:29][Br:28])[N:24]=3)=[CH:16][CH:15]=2)=[C:8]([CH2:9][CH2:10][CH3:11])[C:3]=1[OH:2])(=[O:27])[CH3:26]

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 178439419HCID 178439419, compound

Product 1

HCID 144581835-[(4-((4-Acetyl-3-hydroxy-2-propylphenyl)methoxy)phenyl)]-2-(3-bromopropyl)-2H-tetrazoleYield 82%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-[2-Hydroxy-3-propyl-4-((4-(1H-tetrazol-5-yl)phenoxy)methyl)phenyl]ethanone sodium salt (5 g, 0.013 mol), 1,3-dibromopropane (3.5 g, 0.18 mol), and MEK (50 ml) were combined potassium carbonate (4.15 g, 0.025 mol) potassium was added and the reaction mixture was stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure. The volume of the concentrate was doubled by the addition of water and the resultant solution was extracted with ethyl acetate (3×). The ethylacetate layers were combined, washed with water, dried over sodium 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 5.0 g, 82% yield of the title product: n.m.r. (300 MHz CDCl3) δ: 1.0 (t, 3H); 1.6 (m, 2H); 2.6 (s and t, 5H); 2.7 (t, 2H); 3.5 (t, 2 H); 4.8 (t, 2H); 5.15 (s, 2H); 7.1 (d, 2H); d, 1H); 7.6 (d, 1H); 8.1 (d, 2H); 12.7 (s, 1H).

Workup

  1. additionwas added
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionThe volume of the concentrate was doubled by the addition of water
  4. extractionthe resultant solution was extracted with ethyl acetate (3×)
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed by HPLC (preparatory-scale, silica gel column
  10. washeluted with a mixture of 9:1 toluene

Sources & evidence

ORD record
ord-bc31ecc2e0f94eef8287d81b8fe5dc73
Source dataset
uspto-grants-1989_04
Patent number
US04820722

Reaction notes

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