Ethyl Acetate → 5-Hydroxymethyl-2-[3-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-propyl]-1,2,4-triazole

HRID 741656Notes

Reaction equation

HRID 741656 reaction equation
[C:1]([C:5]1[N:6]=[CH:7][N:8]([CH2:10][CH2:11][CH2:12][O:13][C:14]2[C:19]([CH3:20])=[CH:18][C:17]([C:21]3[N:22]=[N:23][N:24]([CH3:26])[N:25]=3)=[CH:16][C:15]=2[CH3:27])[N:9]=1)(OC)=[O:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].C(OCC)(=O)C>C1COCC1>[OH:2][CH2:1][C:5]1[N:6]=[CH:7][N:8]([CH2:10][CH2:11][CH2:12][O:13][C:14]2[C:15]([CH3:27])=[CH:16][C:17]([C:21]3[N:22]=[N:23][N:24]([CH3:26])[N:25]=3)=[CH:18][C:19]=2[CH3:20])[N:9]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydrideHCID 221033915-Carbomethoxy-2-[3-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]propyl]-1,2,4-triazole

Product 1

HCID 221034215-Hydroxymethyl-2-[3-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-propyl]-1,2,4-triazoleYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 5-carbomethoxy-2-[3-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-propyl]-1,2,4-triazole (37.1 mg, 0.1 mmol) in 1 ml of THF was added at 0° C. a solution of 1M LAH in THF (65 ul, 1M in THF, 0.065 mmol). The mixture was stirred for 10 min at 0° C. and then stirred at 20° C. for 24 h. Rochelle salt solution was added to the mixture and the solution was stirred at 20° C. for 10 min. Ethyl acetate was added to the above mixture, the aqueous layer was extracted with methylene chloride (3×), and the combined organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica column chromatography (10 cm column, ethyl acetate/hexane, 1/1-1/0; methylene chloride/acetone, 2/1-1/2) to afford 27 mg (79%) of 5-hydroxymethyl-2-[3-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-propyl]-1,2,4-triazole, as a white solid.

Workup

  1. stirringstirred at 20° C. for 24 h
  2. stirringthe solution was stirred at 20° C. for 10 min
  3. extractionthe aqueous layer was extracted with methylene chloride (3×)
  4. dry with materialthe combined organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica column chromatography (10 cm column, ethyl acetate/hexane, 1/1-1/0; methylene chloride/acetone, 2/1-1/2)

Sources & evidence

ORD record
ord-eff1dbe8d5c343c0a0dc7c3ba2154a3b
Source dataset
uspto-grants-1996_09
Patent number
US05552420

Reaction notes

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