Water → HCID 178454983, Verbindung

HRID 1599502Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1599502
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1OCC(O)C#C.I[C:14]1[S:18][C:17]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[CH:16][CH:15]=1.[OH-:24].[Na+].[NH4+].[Cl-].[OH2:28]>C1C=CC=CC=1.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:24][C:5]1[CH2:6][O:1][CH:2]=[CH:3][C:4]=1[O:28][C:14]1[SH:18]([C:2]#[C:3][CH2:4][CH3:5])[C:17]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[CH:16][CH:15]=1

Komponenten

10

Edukt 5

HCID 962WaterHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 113237785-Iodo-2,2'-bithiopheneHCID 18920430HCID 18920430, Verbindung

Produkt 1

HCID 178454983HCID 178454983, VerbindungAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 241BenzeneLösungsmittel

Versuchsvorschrift

4-(Tetrahydropyranyloxy)-3-hydroxy-butyne (6.7 g) was dissolved in benzene (20 ml). 5-Iodo-2,2'-bithiophene (5.75 g) was added immediately and stirred. A mixture of CuI (0.15 g) and benzyltriethylammonium chloride (0.14 g, 0.63 mmole) was added. Pd(PPh3)4 (0.46 g, 0.398 mmole) was then added. NaOH solution (30 ml, 2.5N) was added slowly into the mixture at room temperature in water bath for 2 hours. NH4Cl solution (10 ml) was added. The reaction solution was extracted with ethyl acetate. The extract was washed with 10 ml of HCl (10%) for 3 times, 50 ml of water for 3 times and dried over anhydrous magnesium sulfate. The residual solid after evaporation was purified by silica gel column chromatography, eluted with ethyl acetate/n-hexane (1/3). Reddish oily product (6.25 g, 95%) was then obtained.

Aufarbeitung

  1. additionwas added
  2. extractionThe reaction solution was extracted with ethyl acetate
  3. washThe extract was washed with 10 ml of HCl (10%) for 3 times, 50 ml of water for 3 times
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe residual solid after evaporation
  6. customwas purified by silica gel column chromatography
  7. washeluted with ethyl acetate/n-hexane (1/3)

Quellen und Nachweise

ORD-Eintrag
ord-7b2ff702cec74cb8ac034a881d7f6a50
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05741811

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