N,N,N',N'-Tetramethylethylenediamine → HCID 516434、化合物

HRID 1263448ノート

反応式

HRID 1263448 の反応式
[CH2:1]([Li])[CH2:2][CH2:3]C.[CH3:6]CCCCC.CN(C)CCN(C)C.[C:20]([C:23]1[O:24][CH:25]=[CH:26][CH:27]=1)(=O)[CH3:21].C([C:30]12[C:40](C(C)C)=[CH:39][CH:38]=[CH:37][CH:36]1[NH:35][C:34](=O)[O:33][C:31]2=O)C>C1COCC1.[Cl-].[NH4+]>[CH2:34]([N:35]1[C:36]2[C:30](=[CH:40][C:39]([CH:2]([CH3:3])[CH3:1])=[CH:38][CH:37]=2)[C:31](=[O:33])[CH:21]=[C:20]1[C:23]1[O:24][CH:25]=[CH:26][CH:27]=1)[CH3:6]

参加物

8

反応物 5

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8058HexaneHCID 145052-AcetylfuranHCID 86590748HCID 86590748、化合物HCID 178418339Butyllithium

生成物 1

HCID 516434HCID 516434、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 25517Ammonium Chloride溶媒

実験手順

To a 1.6M solution of n-butyl lithium in hexane (1,38 mL, 2,2 mmol) was added tetramethylethylenediamine (0.3 mL, 2,2 mmol) under argon atmosphere at room temperature with stirring. Then 2-acetylfuran (242 mg, 2,2 mmol) in anhydrous THF was added dropwise to the mixture under ice cooling followed by stirring for 1 hour. To this mixture was added 1-ethyl-6-isopropylisatoic anhydride (250 mg, 1.1 mmol) in anhydrous THF. After stirring at room temperature overnight, the reaction mixture was diluted with saturated aqueous solution of ammonium chloride. The resulting organic layer was separated and concentrated under reduced pressure. The residue was dissolved in ethyl acetate and then washed with saturated sodium chloride solution followed by drying with sodium sulfate. After removing ethyl acetate by evaporation in vacuo, the residue was subjected to preparative TLC(n-hexane:ethyl acetate=2:1) to separate the title compound followed by crystallization from diethyl ether. 1H-NMR(CDCl3) δ1.33(6H,d,CH(CH3)2), 1.55(3H,t,CH2CH3), 3.08(1H,septet,CH), 4.17(2H,q,NCH2), 6.48(1H,s,H-3), 6.56-6.58(1H,m,furan H-4′), 6.76(1H,dd,furan H-5′), 7.54(1H,d,H-8), 7.59(1H,dd,H-7), 7.63(1H,dd,furan H-3′), 8.34(1H,d,H-5)

後処理

  1. stirringby stirring for 1 hour
  2. stirringAfter stirring at room temperature overnight
  3. customThe resulting organic layer was separated
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with saturated sodium chloride solution
  7. dry with materialby drying with sodium sulfate
  8. customAfter removing ethyl acetate
  9. customby evaporation in vacuo
  10. customto separate the title compound
  11. customfollowed by crystallization from diethyl ether

出典と根拠

ORDレコード
ord-9024ead57b924b44874c35cfa84422f0
出典データセット
uspto-grants-2003_04
特許番号
US06541470B1

反応ノート

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