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

HRID 505947ノート

反応式

HRID 505947 の反応式
[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

参加物

7

反応物 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 122612,4-DichloropentaneHCID 25517Ammonium ChlorideHCID 178418255HCID 178418255、化合物

生成物 1

HCID 2440144-Phenylpentan-2-ylbenzene

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%.

後処理

  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%

出典と根拠

ORDレコード
ord-ddfcef9722f9420fb90054b2f89f33f2
出典データセット
uspto-grants-2010_08
特許番号
US07781599B2

反応ノート

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