Hydrochloric Acid → Methyl 5-chloro-4-nitroso-5-methylhexanoate

HRID 634894

반응식

HRID 634894 반응식
[N:1]([O:3]CCC(C)C)=O.[CH3:9][C:10]([CH3:18])=[CH:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15].[ClH:19]>>[Cl:19][C:10]([CH3:18])([CH3:9])[CH:11]([N:1]=[O:3])[CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15]

참가 물질

4

반응물 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 10909672Methyl 5-methyl-4-hexenoate

생성물 1

HCID 10058870Methyl 5-chloro-4-nitroso-5-methylhexanoate

반응 조건

온도
-15 °C

실험 절차

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) δ 1.68 & 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 20 (M+H)+.

후처리

  1. temperaturemaintaining the temperature of the reaction mixture below −5° C
  2. additionAfter the addition
  3. filtrationfiltered
  4. washthe precipitate washed with ethanol (−10° C.)
  5. customThe light blue colored solid thus obtained
  6. temperaturecooled to −50° C.
  7. filtrationfiltered

출처 및 근거

ORD 기록
ord-ce88d113a2344aa88f4981eed8d2b581
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06184361B2

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