N,N,N',N'-Tetramethylethylenediamine → 4-Phenylpentan-2-ylbenzene

HRID 505947노트

반응식

HRID 505947 반응식
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN([CH2:12][CH2:13]N(C)C)C.Cl[CH:18]([CH2:20][CH:21](Cl)[CH3:22])[CH3:19].[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[C:1]1([CH:18]([CH2:20][CH:21]([C:13]2[CH:12]=[CH:3][CH:2]=[CH:1][CH:6]=2)[CH3:22])[CH3:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 122612,4-DichloropentaneHCID 25517Ammonium ChlorideHCID 178418255HCID 178418255, 화합물

생성물 1

HCID 2440144-Phenylpentan-2-ylbenzene

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of phenyl magnesium bromide (1.25 mL of 0.96 M THF solution, 1.2 mmol) and TMEDA (181.1 μL, 1.2 mmol) was added to a solution of 2,4-dichloropentane (70.5 mg, 0.5 mmol) and FeCl3 (0.5 mL of 0.1 M THF solution, 0.05 mmol) in THF (0.5 mL) at 50° C. over an hour through a syringe pump. The resulting mixture was stirred at the temperature for 20 minutes and saturated ammonium chloride aqueous solution was added thereto to terminate the reaction, followed by diluting with 3 mL of ethyl acetate. The dilution was filtered through a packed silica gel (eluent: ethyl acetate) followed by concentration under reduced pressure. 1H NMR analysis indicates that the desired product was obtained in almost quantitative yield. Purification by recycling GPC gave the pure compound in a yield of 71%.

후처리

  1. customto terminate
  2. customthe reaction
  3. filtrationThe dilution was filtered through a packed silica gel (eluent: ethyl acetate)
  4. concentrationfollowed by concentration under reduced pressure
  5. customwas obtained in almost quantitative yield
  6. customPurification
  7. customgave the pure compound in a yield of 71%

출처 및 근거

ORD 기록
ord-ddfcef9722f9420fb90054b2f89f33f2
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781599B2

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