Propargyl alcohol → 3-(2-Thienyl)-2-propyn-1-ol

HRID 1093388노트

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HRID 1093388 반응식
I[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:26]([OH:29])[C:27]#[CH:28].C(N(C(C)C)CC)(C)C>[Cu]I.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd].O.O1CCCC1>[S:3]1[CH:4]=[CH:5][CH:6]=[C:2]1[C:28]#[C:27][CH2:26][OH:29]

참가 물질

9

반응물 4

HCID 7859Propargyl alcoholHCID 11776TriphenylphosphineHCID 189212-IodothiopheneHCID 81531Diisopropylethylamine

생성물 1

HCID 110407693-(2-Thienyl)-2-propyn-1-ol

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 2-iodothiophene(5.00 g), copper(I) iodide (91 mg), triphenylphosphine (315 mg), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (497 mg), propargyl alcohol (1.54 ml), diisopropylethylamine (16.6 ml) and tetrahydrofuran (50 ml) was stirred at room temperature for 20 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1-2:1) to give the object product (1.45 g) as a brown oil.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1-2:1)

출처 및 근거

ORD 기록
ord-b4e8221b0e264acea0be1fd76f80a1a4
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129361B2

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