Diisopropylamine → Lithium diisopropylamide

HRID 394275

反応式

HRID 394275 の反応式
[Li:1]CCCC.[CH:6]([NH:9][CH:10]([CH3:12])[CH3:11])([CH3:8])[CH3:7].[C:13]([O:16][CH2:17][CH3:18])(=[O:15])[CH3:14].I[CH2:20][C:21]1[N:22]=[C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[S:24][CH:25]=1>CN1CCCN(C)C1=O.C1COCC1>[Li+:1].[CH3:7][CH:6]([N-:9][CH:10]([CH3:12])[CH3:11])[CH3:8].[CH2:17]([O:16][C:13](=[O:15])[CH2:14][CH2:20][C:21]1[N:22]=[C:23]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[S:24][CH:25]=1)[CH3:18]

参加物

8

反応物 4

HCID 7912DiisopropylamineHCID 8857Ethyl AcetateHCID 131965984-(Iodomethyl)-2-phenylthiazoleHCID 178418339Butyllithium

生成物 2

HCID 2724682Lithium diisopropylamideHCID 686166683-(2-Phenyl-thiazol-4-yl)-propionic acid ethyl ester

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-溶媒

反応条件

温度
-78 °C

実験手順

LDA was prepared by adding 4.7 ml of n-BuLi (1.6 M, hexane) to a solution of 0.76 g (7.5 mmol) of diisopropylamine in 3 ml of abs. THF at −5° C. Then, the mixture was cooled to −78° C., 0.77 g (8.74 mmol) of ethyl acetate were added and the mixture was kept for 15 minutes at that temperature to ensure complete deprotonation. Afterwards, 0.79 g (2.5 mmol) of 4-iodomethyl-2-phenyl-thiazole dissolved in 5 ml of abs. THF and 3 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinon (DMPU) were added and stirring was continued for 0.5 hours at −78° C. Then, the reaction mixture was quenched with ammonium chloride solution, extracted twice with AcOEt, washed with water, dried over anhydrous sodium sulfate, and evaporated to dryness. The residue was chromatographed on silicagel with dichloromethane as eluent. 0.46 g of 3-(2-phenyl-thiazol-4-yl)-propionic acid ethyl ester were obtained as light yellow liquid (70% of theory).

後処理

  1. customat −5° C
  2. waitwas continued for 0.5 hours at −78° C
  3. customThen, the reaction mixture was quenched with ammonium chloride solution
  4. extractionextracted twice with AcOEt
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated to dryness
  8. customThe residue was chromatographed on silicagel with dichloromethane as eluent

出典と根拠

ORDレコード
ord-4651043e0a9f4b7fb5abe05bc419df7a
出典データセット
uspto-grants-2004_10
特許番号
US06809110B2

関連ノート

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