tert-Butyl mercaptan → Ethyl 5-(tert-butylsulfanyl)-2,2-dimethyl-4-oxopentanoate

HRID 1620804노트

반응식

HRID 1620804 반응식
O1CCCC1.[CH2:6]([O:8][C:9](=[O:18])[C:10]([CH3:17])([CH3:16])[CH2:11][C:12](=[O:15])[CH2:13]Br)[CH3:7].[CH3:19][C:20]([SH:23])([CH3:22])[CH3:21].C(N(CC)CC)C>CCCCCC>[CH2:6]([O:8][C:9](=[O:18])[C:10]([CH3:17])([CH3:16])[CH2:11][C:12](=[O:15])[CH2:13][S:23][C:20]([CH3:22])([CH3:21])[CH3:19])[CH3:7]

참가 물질

6

반응물 4

HCID 6387tert-Butyl mercaptanHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 4090969Ethyl 5-bromo-2,2-dimethyl-4-oxopentanoate

생성물 1

HCID 3576811Ethyl 5-(tert-butylsulfanyl)-2,2-dimethyl-4-oxopentanoate

시약·촉매·용매 1

HCID 8058Hexane용매

반응 조건

온도
-2.5 °C

실험 절차

To a reaction flask containing tetrahydrofuran (5.0-fold, V/W of starting material) was added 5-bromo-2,2-dimethyl-4-oxo-pentanoic acid ethyl ester (1.0 eq) under nitrogen. The mixture was cooled to a temperature of −5-0° C., and a solution of 2-methyl-2-propanethiol (1.2 eq) and triethylamine (1.25 eq) was added while maintaining the temperature below 0° C. The reaction was stirred at room temperature for 25 hours, and then hexane (3.0-fold, V/W of starting material) was slowly added. After agitating for 30 minutes, the solid material was removed by filtration and washed with 50% ethyl acetate/hexane solution. The filtrate was concentrated under reduced pressure to give the desired product, which was taken on to the next step without further purification.

후처리

  1. temperaturewhile maintaining the temperature below 0° C
  2. stirringAfter agitating for 30 minutes
  3. customthe solid material was removed by filtration
  4. washwashed with 50% ethyl acetate/hexane solution
  5. concentrationThe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-3f005074dc9648be948a40463512051c
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772495B2

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