N,N,N',N'-Tetramethylethylenediamine → HCID 516472、化合物

HRID 1263456ノート

反応式

HRID 1263456 の反応式
C([Li])CCC.CCCCCC.CN(CCN(C)C)C.[CH3:20][C:21]1[S:25][C:24]2[C:26](=O)[CH2:27][CH2:28][C:23]=2[CH:22]=1.[CH2:30]([N:32]1[C:41]2[C:36](=[CH:37][C:38]([CH:42]([CH3:44])[CH3:43])=[CH:39][CH:40]=2)[C:35](=[O:45])C=C1C1OC=CC=1)[CH3:31]>C1COCC1.[Cl-].[NH4+]>[CH2:30]([N:32]1[C:41]2[C:36](=[CH:37][C:38]([CH:42]([CH3:44])[CH3:43])=[CH:39][CH:40]=2)[C:35](=[O:45])[C:27]2[CH2:28][C:23]3[CH:22]=[C:21]([CH3:20])[S:25][C:24]=3[C:26]1=2)[CH3:31]

参加物

8

反応物 5

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8058HexaneHCID 516434HCID 516434、化合物HCID 12416658HCID 12416658、化合物HCID 178418339Butyllithium

生成物 1

HCID 516472HCID 516472、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 1.53M solution of n-butyl lithium in hexane (0.47 mL, 0.72 mmol) were added under argon atmosphere TMEDA (0.11 mL, 0.72 mmol) at room temperature and then 2-methyl-4,5-dihydro-6H-cyclopenta[b]thiophen-6-one (0.11 g, 0.72 mmol) in anhydrous THF dropwise with ice cooling and stirring. The reaction mixture was stirred at room temperature for 1 hour and ice-cooled again. To this was added dropwise a solution of 1-ethyl-6-isopropylisatoic anhydride (Example 6, step 1) (0.11 g, 0.48 mmol) in anhydrous THF. The reaction mixture was stirred at room temperature for 2 hours and diluted with saturated aqueous solution of ammonium chloride. The organic layer was concentrated to dryness and the residue was dissolved in ethyl acetate. This solution was washed with saturated sodium chloride solution, dried with sodium sulfate and evaporated again. The residue was subjected to silica gel-chromatography (chloroform: acetone=9:1) and crystallization from diethyl ether to give the title compound. 1H-NMR(CDCl3) δ 1.33(6H,d,CH(CH3)2), 1.58(3H,t,CH2CH3), 2.64(3H,s,CH3), 3.10(1H,septet,CH), 3,78(2H,s,H-4), 4,49(2H,q,NCH3), 6.97(1H,s,H-3), 7.49(1H,d,H-9), 7.56(1H,dd,H-8), 8.45(1H,d,H-6)

後処理

  1. temperatureice-cooled again
  2. stirringThe reaction mixture was stirred at room temperature for 2 hours
  3. concentrationThe organic layer was concentrated to dryness
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThis solution was washed with saturated sodium chloride solution
  6. dry with materialdried with sodium sulfate
  7. customevaporated again
  8. customThe residue was subjected to silica gel-chromatography (chloroform: acetone=9:1) and crystallization from diethyl ether

出典と根拠

ORDレコード
ord-59b0ee803f754595a5e739387a5e3803
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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