Реакция #75439

Уравнение реакции

isoamyl nitrite

methyl 5-methyl-4-hexenoate

HCl

→

title product

Methyl 5-chloro-4-nitroso-5-methylhexanoate

Растворители

Условия реакции

Обработка

1. 1
   Температураmaintaining the temperature of the reaction mixture below −5° C
2. 2
   workup.ADDITIONAfter the addition
3. 3
   Фильтрацияfiltered
4. 4
   Промывкаthe precipitate washed with ethanol (−10° C.)
5. 5
   ДругоеThe light blue colored solid thus obtained
6. 6
   Температураcooled to ˜−50° C.
7. 7
   Фильтрацияfiltered

Методика

A mixture of isoamyl nitrite (12 mL) and methyl 5-methyl-4-hexenoate (4.90 g, 35.00 mmol) was cooled to −15° C. To this stirred solution, concentrated HCl (12.5 mL) was added dropwise from an addition flask maintaining the temperature of the reaction mixture below −5° C. After the addition, the reaction mixture was stirred at 0° C. for 30 minutes, filtered and the precipitate washed with ethanol (−10° C.). The light blue colored solid thus obtained was dispersed in petroleum ether (50 mL), cooled to ˜−50° C. and filtered to provide the title product as a colorless solid. Yield: 3.0 g (41.3%); m.p. 90-91° C. 1H NMR (CDCl3) δ1.68 & 1.71[2s, 6H, C(CH3)2], 2.35[m, 4H, (CH2)2], 3.73(s, 3H, COOCH3) and 5.11(t, 1H, CH). MS m/e 208 (M+H)+.

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