Propargyl alcohol → (E)-6,6-dimethyl-4-hepten-2-yn-1-ol

HRID 1464782

反応式

HRID 1464782 の反応式
I/[CH:2]=[CH:3]/[C:4]([CH3:7])([CH3:6])[CH3:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N)CCC.[CH2:32]([OH:35])[C:33]#[CH:34]>O1CCCC1.[Cu]I.[Pd](Cl)Cl.C(OCC)(=O)C.O>[CH3:5][C:4]([CH3:7])([CH3:6])/[CH:3]=[CH:2]/[C:34]#[C:33][CH2:32][OH:35]

参加物

10

反応物 4

HCID 7859Propargyl alcoholHCID 8007ButylamineHCID 11776TriphenylphosphineHCID 11063689(E)-1-iodo-3,3-dimethylbut-1-ene

生成物 1

HCID 19917005(E)-6,6-dimethyl-4-hepten-2-yn-1-ol

試薬・触媒・溶媒 5

HCID 24290Palladium Chloride触媒HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

0.63 g of (E)-1- iodo-3,3-dimethyl-1-butene [see J. Org. Chem., 43, 4424 (1978)] was dissolved in 10 ml of tetrahydrofuran, and 31 mg of triphenylphosphine, 29 mg of copper(I) iodide, 11 mg of palladium chloride, 1.5 ml of n-butylamine and 0.35 ml of propargyl alcohol were added. The mixture was stirred overnight at room temperature, and then water and ethyl acetate were added. The organic layer separated was worked up in a customary manner, and the product was purified by silica gel column chromatography [hexane/ethyl acetate=2/1] to give 0.27 g of the captioned compound as a pale brown oil.

後処理

  1. customThe organic layer separated
  2. customthe product was purified by silica gel column chromatography [hexane/ethyl acetate=2/1]

出典と根拠

ORDレコード
ord-8bfc60aedb7d4839b58de804983eda20
出典データセット
uspto-grants-1994_04
特許番号
US05306728

関連ノート

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