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

HRID 2366090ノート

反応式

HRID 2366090 の反応式
C1COCC1.[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 THF (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 N2. 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% EtOAc/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% EtOAc/hexane solution
  5. concentrationThe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-4f5c98ad0d624c1ab246a3dca2f5a189
出典データセット
uspto-grants-2014_04
特許番号
US08697730B2

反応ノート

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