1,3-Dibromopropane → 5-[(4-((4-Acetyl-3-hydroxy-2-propylphenyl)methoxy)phenyl)methyl]-2-(3-bromopropyl)-2H-tetrazole

HRID 620238Notes

Reaction equation

HRID 620238 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]([CH2:20][C:21]3[NH:25][N:24]=[N:23][N:22]=3)=[CH:16][CH:15]=2)[CH:6]=[CH:5][C:4]=1[C:26](=[O:28])[CH3:27].[OH-].[Na+].[Br:31][CH2:32][CH2:33][CH2:34]Br>C1COCC1>[C:26]([C:4]1[CH:5]=[CH:6][C:7]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]3[N:22]=[N:23][N:24]([CH2:34][CH2:33][CH2:32][Br:31])[N:25]=3)=[CH:16][CH:15]=2)=[C:8]([CH2:9][CH2:10][CH3:11])[C:3]=1[OH:2])(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 14798Sodium HydroxideHCID 178439421HCID 178439421, compound

Product 1

HCID 144581665-[(4-((4-Acetyl-3-hydroxy-2-propylphenyl)methoxy)phenyl)methyl]-2-(3-bromopropyl)-2H-tetrazoleYield 15.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-[2-Hydroxy-3-propyl-4-((4-(1H-tetrazol-5-ylmethyl)phenoxy)methyl)phenyl]ethanone sodium salt (15 g, 0.039 mol) was added to THF (150 ml) and the minimum amount of lN sodium hydroxide soluton was added to effect solution. 1,3-Dibromopropane (12.12 g, 0.06 mol) was added and the reaction solution was stirred at room temperature for 24 hours. The reaction mixuture was concentrated in vacuo. Water was added to the concentrate and the resultant mixture was extracted with ethyl acetate (3×). The organic layers were combined, washed with water, dried over sodium sulfate, filtered, and concentrated. The resultant residue was chromatographed by HPLC on a silica gel column eluted with a mixture of 9:1 toluene:ethyl acetate to yield 3.0 g of a light yellow oil of the 2H-tetrazole-2-isomer of the above product.

Workup

  1. concentrationThe reaction mixuture was concentrated in vacuo
  2. additionWater was added to the
  3. concentrationconcentrate
  4. extractionthe resultant mixture was extracted with ethyl acetate (3×)
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resultant residue was chromatographed by HPLC on a silica gel column
  10. washeluted with a mixture of 9:1 toluene

Sources & evidence

ORD record
ord-a4622bd03d354f47be43e3cd096e1901
Source dataset
uspto-grants-1989_04
Patent number
US04820722

Reaction notes

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