반응 #74589

반응 방정식

tert-Butyl 3-(2-{[tert-butyl(dimethyl)silyl]oxy}-5-chlorophenyl)azetidine-1-carboxylate

tetramethylammonium fluoride

→

title compound

수율 38.0%

tert-Butyl 3-(5-chloro-2-hydroxyphenyl)azetidine-1-carboxylate

수율 38.0%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   농축before concentrating in vacuo
2. 2
   기타The residue was partitioned between tert-butyl methyl ether (100 ml) and aqueous sodium hydroxide solution
3. 3
   건조The organics were dried over sodium sulfate
4. 4
   여과filtered
5. 5
   기타evaporated in vacuo
6. 6
   기타to give a reddish brown oil, 2.33 g
7. 7
   기타This was purified by column chromatography (100 g of silica)
8. 8
   세척eluting with heptane:ethyl acetate (6:4, by volume)

실험 절차

To a solution of tert-Butyl 3-(2-{[tert-butyl(dimethyl)silyl]oxy}-5-chlorophenyl)azetidine-1-carboxylate (Preparation 238, 3.1 g, 7.79 mmol) in tetrahydrofuran (80 ml) was added tetramethylammonium fluoride (1.0 g, 10.74 mmol). The mixture was stirred at room temperature for 18 hours before concentrating in vacuo. The residue was partitioned between tert-butyl methyl ether (100 ml) and aqueous sodium hydroxide solution. The organics were dried over sodium sulfate, filtered and evaporated in vacuo to give a reddish brown oil, 2.33 g. This was purified by column chromatography (100 g of silica) eluting with heptane:ethyl acetate (6:4, by volume) to afford the title compound as a reddish brown gum, 850 mg, 38% yield.

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