Water → HCID 23081182, compound

HRID 856036Notes

Reaction equation

HRID 856036 reaction equation
C([Li])CCC.[CH2:6]([N:8]1[C:12]([CH3:13])=[N:11][N:10]=[N:9]1)[CH3:7].Cl[CH2:15][C:16]([CH3:18])=[CH2:17].O>C1COCC1>[CH2:6]([N:8]1[C:12]([CH2:13][CH2:17][C:16]([CH3:18])=[CH2:15])=[N:11][N:10]=[N:9]1)[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 112413-Chloro-2-methyl-1-propeneHCID 126931921-Ethyl-5-methyl-1H-tetrazoleHCID 178418339Butyllithium

Product 1

HCID 23081182HCID 23081182, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

n-Butyl lithium (1.53 M) hexane solution (6.5 ml, 9.98 mmol) was added dropwise to a solution of 1-ethyl-5-methyl-1H-tetrazole (0.80 g, 7.13 mmol) in THF (15 ml) while stirring at −70° C., and the mixture was further stirred for 1.5 hours. A solution of 3-chloro-2-methyl-1-propene (0.77 ml, 7.84 mmol) in THF (5 ml) was added to the mixture, and the resulting mixture was stirred for 2 hours. Water was added to the reaction mixture, the resulting mixture was extracted with ethyl acetate, and the extract was dried over magnesium sulfate, and then concentrated under reduced pressure to afford 1-ethyl-5-(3-methyl-3-butenyl)-1H-tetrazole (0.95 g, yield 80%) as a brown oil.

Workup

  1. stirringthe mixture was further stirred for 1.5 hours
  2. stirringthe resulting mixture was stirred for 2 hours
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. dry with materialthe extract was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bd86af8b84e5438ea5e5b06d0d68af1c
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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