Methanesulfonic Acid → 2-(2-Tert-butyl-tetrazol-5-yl)-benzaldehyde

HRID 1068926Notes

Reaction equation

HRID 1068926 reaction equation
[NH:1]1[C:5]([C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[CH:8]=[O:9])=[N:4][N:3]=[N:2]1.[CH2:14]=[C:15]([CH3:17])[CH3:16].CS(O)(=O)=O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:15]([N:3]1[N:2]=[N:1][C:5]([C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[CH:8]=[O:9])=[N:4]1)([CH3:17])([CH3:16])[CH3:14]

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 8255IsobutyleneHCID 178519511HCID 178519511, compound

Product 1

HCID 211906522-(2-Tert-butyl-tetrazol-5-yl)-benzaldehyde

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In an autoclave, 6.4 g (36.7 mmol) of 2-(tetrazol-5-yl)-benzaldehyde (Step 61.1) in 50 ml of toluene are heated at 110° C. for 1.5 hours with ≈3 g of isobutene and 0.432 ml of methanesulfonic acid. When cold the reaction mixture is diluted with 300 ml of ethyl acetate, washed four times with water and once with brine, dried (Na2SO4) and concentrated by evaporation. Column chromatography (SiO2; hexane/ethyl acetate=4:1) and crystallization from hexane with a small amount of diethyl ether at −20° C. yield 2-(2-tert-butyl-tetrazol-5-yl)-benzaldehyde; TLC: Rf=0.36 (hexane/ethyl acetate=10:1).

Workup

  1. washwashed four times with water
  2. dry with materialonce with brine, dried (Na2SO4)
  3. concentrationconcentrated by evaporation
  4. customColumn chromatography (SiO2; hexane/ethyl acetate=4:1) and crystallization from hexane with a small amount of diethyl ether at −20° C.

Sources & evidence

ORD record
ord-108f0cb0719a4ac59690329c82670420
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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