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

HRID 1068926노트

반응식

HRID 1068926 반응식
[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]

참가 물질

6

반응물 3

HCID 6395Methanesulfonic AcidHCID 8255IsobutyleneHCID 178519511HCID 178519511, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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.

출처 및 근거

ORD 기록
ord-108f0cb0719a4ac59690329c82670420
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06251911B1

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