N,N,N',N'-Tetramethylethylenediamine → HCID 9905607, 화합물

HRID 1263449노트

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HRID 1263449 반응식
C([Li])CCC.CCCCCC.CN(CCN(C)C)C.[CH2:20]([C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[C:27](=O)[CH2:26][CH2:25]2)[CH3:21].[CH2:32]([N:34]1[C:43]2[C:38](=[CH:39][C:40]([CH:44]([CH3:46])[CH3:45])=[CH:41][CH:42]=2)[C:37](=[O:47])C=C1C1OC=CC=1)[CH3:33]>C1COCC1.[Cl-].[NH4+]>[CH2:20]([C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[C:27]1[N:34]([CH2:32][CH3:33])[C:43]3[CH:42]=[CH:41][C:40]([CH:44]([CH3:45])[CH3:46])=[CH:39][C:38]=3[C:37](=[O:47])[C:26]=1[CH2:25]2)[CH3:21]

참가 물질

8

반응물 5

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8058HexaneHCID 516434HCID 516434, 화합물HCID 110519505-ETHYL-2,3-DIHYDRO-1H-INDEN-1-ONEHCID 178418339Butyllithium

생성물 1

HCID 9905607HCID 9905607, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 25517Ammonium Chloride용매

실험 절차

To a 1.53M solution of n-butyl lithium in hexane (13.2 mL, 20.2 mmol) was added TMEDA (3.1 mL, 20.2 mmol) under argon atmosphere at room temperature with stirring. To this was added with ice cooling a solution of 5-ethyl-1-indanone(3.24 g, 20.2 mmol) in anhydrous THF followed by stirring at room temperature for 1 hour. After ice cooling the mixture, a solution of 1-ethyl-6-isopropylisatoic anhydride (Example 6, step 1) (2.35 g, 10.1 mmol) in anhydrous THF was added dropwise thereto. The mixture was stirred at room temperature overnight and diluted with saturated aqueous solution of ammonium chloride. The orgaic layer was separated and concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with saturated sodium chloride solution and dried with sodium sulfate. After removing the solvent, the residue was purified by silica gel-chromatography (chloroform:acetone=20:1) and crystallization from diethyl ether to give the desired compound. 1H-NMR(CDCl3) δ 1.32(3H,t,CH2CH3), 1.34(6H,d,CH(CH3)2), 1.70(3H,t,NCH2CH3), 2.78(2H,q,CH2CH3), 3.10(1H,septet,CH), 3.91(2H,s,H-11), 4.72(2H,q,NCH2), 7.30-7.85(5H,m,Ar-H), 8.45(1H,s,H-9)

후처리

  1. stirringby stirring at room temperature for 1 hour
  2. stirringThe mixture was stirred at room temperature overnight
  3. customThe orgaic layer was separated
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with saturated sodium chloride solution
  7. dry with materialdried with sodium sulfate
  8. customAfter removing the solvent
  9. customthe residue was purified by silica gel-chromatography (chloroform:acetone=20:1) and crystallization from diethyl ether

출처 및 근거

ORD 기록
ord-313a6d429cae425989a3c6d44804f7ab
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06541470B1

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