1-Ethynyl-4-methoxybenzene → 1-[4-(4-Methoxyphenylethynyl)phenoxy]-2-diethylaminoethane

HRID 1648721

反応式

HRID 1648721 の反応式
Br[C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][CH2:8][N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])=[CH:4][CH:3]=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[CH:25])=[CH:20][CH:19]=1>C(N(CC)CC)C.[Pd].[Cu]I>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[C:25][C:2]2[CH:15]=[CH:14][C:5]([O:6][CH2:7][CH2:8][N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])=[CH:4][CH:3]=2)=[CH:20][CH:19]=1

参加物

6

反応物 2

HCID 2510201-Ethynyl-4-methoxybenzeneHCID 4239532-(4-bromophenoxy)-N,N-diethylethanamine

生成物 1

HCID 204815621-[4-(4-Methoxyphenylethynyl)phenoxy]-2-diethylaminoethane収率 80%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8471Triethylamine溶媒

実験手順

To a solution of 15 g (0.06 mole) of 1-(4-bromophenoxy)-2-diethylaminoethane and 8.2 g (0.062 mole) of 4-methoxyphenylacetylene in 150 ml of triethylamine are added, under nitrogen, 420 mg of the palladium complex PdCl2 [P(C6H5)2 ]2 and 228 mg of copper(I) iodide. The reaction mixture is subsequently refluxed for 24 hours, then concentrated, and the residue is taken up in water. After extraction with 200 ml of ether, the combined ethereal phases are washed 3 times with water, dried and evaporated to dryness. The crude product is chromatographed on silica gel, affording 15.5 g (80%) of 1-[4-(4-methoxyphenylethynyl)phenoxy]-2-diethylaminoethane with a melting point of 59°-60° C.

後処理

  1. temperatureThe reaction mixture is subsequently refluxed for 24 hours
  2. concentrationconcentrated
  3. extractionAfter extraction with 200 ml of ether
  4. washthe combined ethereal phases are washed 3 times with water
  5. customdried
  6. customevaporated to dryness
  7. customThe crude product is chromatographed on silica gel

出典と根拠

ORDレコード
ord-2a39689c8236429aa40f690711c5e80e
出典データセット
uspto-grants-1983_11
特許番号
US04412856

関連ノート

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