반응 #669346

반응 방정식

1-trityl-3-iodo-1,2,4-triazole

propargyl alcohol

triethylamine

water

→

1-hydroxy-3(1-trityl-1,2,4-triazol-3-yl)prop-2-yne

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.WAITto stand overnight
2. 2
   workup.STIRRINGStirring
3. 3
   기타was continued for a further four periods of seven hours
4. 4
   추출extracted with chloroform (5×250 ml)
5. 5
   건조The extracts were dried over magnesium sulphate
6. 6
   기타evaporated under reduced pressure
7. 7
   기타chromatographed on silica

실험 절차

A stirred solution of 1-trityl-3-iodo-1,2,4-triazole (26.24 g, prepared as described in Example 5), propargyl alcohol (3.56 ml) and triethylamine (40 ml) in dry N,N-dimethylformamide (750 ml) was treated successively with tetrakis(triphenylphosphine)palladium (2.77 g) and cuprous iodide (1.0 g). It was stirred for four hours at room temperature under nitrogen and allowed to stand overnight but the reaction had not proceeded to completion. Stirring was continued for a further four periods of seven hours, then the mixture was poured into water (1 l) and extracted with chloroform (5×250 ml). The extracts were dried over magnesium sulphate, evaporated under reduced pressure and chromatographed on silica, using ethyl acetate-hexane (4:1) as eluant. Trituration with ether gave 1-hydroxy-3(1-trityl-1,2,4-triazol-3-yl)prop-2-yne (12.20 g). Recrystallisation from chloroform gave material m.p. 211° C. NMR (CDCl3): δ 4.45(2H,s), 7.1-7.3(15H,m), 7.95(1H,s). 13C NMR provided confirmation. M/S: M+ 365.

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