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

HRID 1648721

반응식

HRID 1648721 반응식
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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8471Triethylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2a39689c8236429aa40f690711c5e80e
출처 데이터셋
uspto-grants-1983_11
특허 번호
US04412856

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