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

HRID 1620804ノート

反応式

HRID 1620804 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

反応条件

温度
-2.5 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3f005074dc9648be948a40463512051c
出典データセット
uspto-grants-2014_07
特許番号
US08772495B2

反応ノート

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