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

HRID 1464782

반응식

HRID 1464782 반응식
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]

참가 물질

10

반응물 4

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

생성물 1

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

시약·촉매·용매 5

HCID 24290Palladium Chloride촉매HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-8bfc60aedb7d4839b58de804983eda20
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05306728

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