Acetonitrile → 2-[4-[(6-Bromohexyl)oxy]butyl]-N,N-diethylbenzamide

HRID 1721912ノート

反応式

HRID 1721912 の反応式
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]#[CH:12].[CH2:13]([N:15]([CH2:25][CH3:26])[C:16](=[O:24])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1I)[CH3:14].C1(NC2CCCCC2)CCCCC1.C(#N)C>CCOCC.[Cu]I>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:22]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:16]([N:15]([CH2:13][CH3:14])[CH2:25][CH3:26])=[O:24]

参加物

7

反応物 4

HCID 6342AcetonitrileHCID 7582DicyclohexylamineHCID 789049N,N-Diethyl-2-iodobenzamideHCID 113792816-Bromohexylbut-3-ynyl ether

生成物 1

HCID 200298332-[4-[(6-Bromohexyl)oxy]butyl]-N,N-diethylbenzamide

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 3283Diethyl Ether溶媒

実験手順

A mixture of CuI (20 mg), 1-bromo-6-[(3-butynyl)oxyl]hexane (3.04 g), N,N-diethyl-2-iodobenzamide (3.95 G), BTPC (200 mg), N,N-dicyclohexylamine (2.60 g) and acetonitrile (20 ml) was stirred under nitrogen at room temperature for 4.5 h, diluted with ether (200 ml) and filtered. The filtrate was evaporated in vacuo, the residue in ethanol (100 ml) was treated with charcoal and the solvent evaporated in vacuo. The residual oil (5.32 g) in absolute ethanol (190 ml) was hydrogenated over pre-reduced 10% PDO-C (50% paste in water, 1.25 g) in absolute ethanol (20 ml), filtered through hyflo and evaporated in vacuo to give an oil. Purification by FCC eluting with T-EA-triethylamine (95:5:1) followed by FCC eluting with CX-EA (2:1) gave the title compound as a yellow oil (2.04 g). T.l.c. (T-ET-A-40:10:1) Rf 0.14.

後処理

  1. filtrationfiltered
  2. customThe filtrate was evaporated in vacuo
  3. additionthe residue in ethanol (100 ml) was treated with charcoal
  4. customthe solvent evaporated in vacuo
  5. filtrationfiltered through hyflo
  6. customevaporated in vacuo
  7. customto give an oil
  8. customPurification by FCC
  9. washeluting with T-EA-triethylamine (95:5:1)
  10. washeluting with CX-EA (2:1)

出典と根拠

ORDレコード
ord-a827614f267048adb2b2ab770030ac75
出典データセット
uspto-grants-1989_08
特許番号
US04853382

反応ノート

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