Diethyl Ether → (trans)-3-(7-Phenyl-1,2-heptadiene-4,6-diynyl)oxiranemethanol

HRID 280394

Reaktionsgleichung

Reaktionsgleichung von HRID 280394
[CH2:1](O)/[CH:2]=[CH:3]/[CH2:4][OH:5].[C:7]1([CH3:17])[CH:12]=[CH:11][C:10](S(O)(=O)=O)=[CH:9][CH:8]=1.O1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19]1.CC[O:26]CC>>[C:7]1([C:17]#[C:19][C:20]#[C:21][CH:22]=[C:23]=[CH:1][C@@H:2]2[O:26][C@H:3]2[CH2:4][OH:5])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

5

Edukt 4

HCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 175854trans-2-Butene-1,4-diol

Produkt 1

HCID 86740795(trans)-3-(7-Phenyl-1,2-heptadiene-4,6-diynyl)oxiranemethanol

Versuchsvorschrift

To a solution of trans-2-butene-1,4-diol (7.57 g, 85.9 mmole) and a catalytic quantity of p-toluenesulfonic acid in 700 ml of dry ether was added dihydropyran (6.73 ml, 71.6 mmole) at the rate of 1.5 ml/hour. After stirring for four days, the reaction mixture was washed with saturated sodium bicarbonate, and the organic layer was separated and dried over sodium sulfate and concentrated in vacuo to afford the crude product which was purified via flash chromatography (LPS-1 silica gel; ether-hexane 1:1) to provide the title compound (5.75 g).

Aufarbeitung

  1. washthe reaction mixture was washed with saturated sodium bicarbonate
  2. customthe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto afford the crude product which
  6. customwas purified via flash chromatography (LPS-1 silica gel; ether-hexane 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-1d627643a6b3400ab96df2d3cc7f0861
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04588828

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