Tetrahydrofuran → 1,1-Bis(3,5-dimethoxyphenyl)prop-2-yn-1-ol

HRID 883828

Reaktionsgleichung

Reaktionsgleichung von HRID 883828
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:13]2[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[CH:14]=2)=[O:12])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[CH2:23]1COC[CH2:24]1.C([Mg]Br)#C.CC(C)=O.CCCCCC>C(OCC)C>[CH3:22][O:21][C:15]1[CH:14]=[C:13]([C:11]([C:5]2[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)([OH:12])[C:23]#[CH:24])[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 21609692Bis(3,5-dimethoxyphenyl)methanone2×HCID 21880519Acetone hexaneHCID 178418486HCID 178418486, Verbindung

Produkt 1

HCID 866533821,1-Bis(3,5-dimethoxyphenyl)prop-2-yn-1-olAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

In a 100 mL flask, bis(3,5-dimethoxy-phenyl)methanone (compound B, 1.2 g, 3.9 mmol) was dissolved in 20 mL diethyl ether. Approximately 5 mL THF was added to help solvate the ketone followed by the slow addition of ethynylmagnesium bromide (0.5 M in THF, 12 mL). The reaction was monitored by TLC and upon consumption of starting material, 2N HCl was added to the flask. The mixture was extracted 3 times with ethyl acetate and the combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered, and concentrated to give a yellow oil. Purification was achieved with column chromatography using a gradient of 30% to 50% acetone/hexane. The product was obtained as a pale yellow oil in 73% yield: Rf 0.14 (30:70 acetone/hexane); IR (cm−1): 3441, 3280, 2940, 2837, 1598, 1460, 1289, 1205, 1156, 1053, 834, 748, 689; 1H NMR (250 MHz, C6D6): δ 2.38 (s, 1H), 2.94 (br s, 1H), 3.27 (s, 12H), 6.42 (t, J=2.5 Hz, 2H), 3.99 (d, J=2.5 Hz, 4H); 13C NMR (63 MHz, C6D6): 54.8 (4C), 74.5, 75.3, 86.8, 100.1 (2C), 104.9 (4C), 147.6 (2C), 161.2 (4C).

Aufarbeitung

  1. customThe reaction was monitored by TLC and upon consumption of starting material, 2N HCl
  2. additionwas added to the flask
  3. extractionThe mixture was extracted 3 times with ethyl acetate
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a yellow oil
  9. customPurification
  10. customThe product was obtained as a pale yellow oil in 73% yield

Quellen und Nachweise

ORD-Eintrag
ord-eaf6942f67154710a51de840aea96f02
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08237003B2

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