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

HRID 2293895

反応式

HRID 2293895 の反応式
[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]

参加物

4

反応物 3

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

生成物 1

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

反応条件

温度
-15 °C

実験手順

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 208 (M+H)+.

後処理

  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

出典と根拠

ORDレコード
ord-e6b1c812b3214ddea090f9d88f3187f4
出典データセット
uspto-grants-1997_11
特許番号
US05688487

関連ノート

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