Diisopropylamine → Lithium diisopropylamide

HRID 394275

반응식

HRID 394275 반응식
[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]

참가 물질

8

반응물 4

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

생성물 2

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-용매

반응 조건

온도
-78 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4651043e0a9f4b7fb5abe05bc419df7a
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809110B2

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