Propargyl alcohol → 3-(5-Methyl-2-thienyl)-2-propyne-1-ol

HRID 1093394

反応式

HRID 1093394 の反応式
I[C:2]1[S:3][C:4]([CH3:7])=[CH:5][CH:6]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:27]([OH:30])[C:28]#[CH:29].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>[CH3:7][C:4]1[S:3][C:2]([C:29]#[C:28][CH2:27][OH:30])=[CH:6][CH:5]=1

参加物

9

反応物 4

HCID 7859Propargyl alcoholHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 1400962-Iodo-5-methylthiophene

生成物 1

HCID 594075163-(5-Methyl-2-thienyl)-2-propyne-1-ol

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 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)触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 2-iodo-5-methylthiophene (5.00 g), copper(I) iodide (82 mg), triphenylphosphine (286 mg), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (445 mg), propargyl alcohol (1.91 ml), diisopropylethylamine (15.1 ml) and tetrahydrofuran (30 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 (1.48 g) as a brown oil.

後処理

  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)

出典と根拠

ORDレコード
ord-39f77001690a4a04b01060a72968ea12
出典データセット
uspto-grants-2012_03
特許番号
US08129361B2

関連ノート

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