Sodium ethanethiolate → Methyl 4-[3-(ethylthio)propyl]bicyclo[2.2.2]octane-1-carboxylate

HRID 22858

반응식

HRID 22858 반응식
CS(O[CH2:6][CH2:7][CH2:8][C:9]12[CH2:16][CH2:15][C:12]([C:17]([O:19][CH3:20])=[O:18])([CH2:13][CH2:14]1)[CH2:11][CH2:10]2)(=O)=O.[CH2:21]([S-:23])[CH3:22].[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH2:21]([S:23][CH2:6][CH2:7][CH2:8][C:9]12[CH2:16][CH2:15][C:12]([C:17]([O:19][CH3:20])=[O:18])([CH2:13][CH2:14]1)[CH2:11][CH2:10]2)[CH3:22]

참가 물질

5

반응물 2

HCID 4459711Sodium ethanethiolateHCID 22591707Methyl 4-{3-[(methylsulfonyl)oxy]propyl}bicyclo-[2.2.2]octane-1-carboxylate

생성물 1

HCID 22591678Methyl 4-[3-(ethylthio)propyl]bicyclo[2.2.2]octane-1-carboxylate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
45 °C

실험 절차

Mesylate 11-5 (3.30 g, 10.9 mmol) was dissolved in DMF (20 mL) and treated with sodium ethanethiolate (1.82 g, 21.7 mmol). The solution was stirred at 45° C. for 3 h, then the mixture was diluted with 100 mL of ethyl acetate and washed twice with 1N aqueous HCl, then with saturated aqueous sodium bicarbonate, and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated to afford methyl 4-[3-(ethylthio)propyl]bicyclo[2.2.2]octane-1-carboxylate (11-6) as a crude oil which was used without purification in the next step.

후처리

  1. washwashed twice with 1N aqueous HCl
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customevaporated

출처 및 근거

ORD 기록
ord-26694abd109b440680ad6c823d5c4748
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849636B2

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