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Propargyl alcohol → [3-(3-Hydroxyprop-1-ynyl)phenoxy]acetic acid tert-butyl ester

HRID 1352863
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1352863
I[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[O:5][CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[CH2:17]([OH:20])[C:18]#[CH:19].C(OCC)(=O)C>C(N(CC)CC)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:20][CH2:17][C:18]#[C:19][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[O:5][CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 7859Propargyl alcoholHCID 8857Ethyl AcetateHCID 52449400t-Butyl (3-iodophenoxy)acetate

Produkt 1

HCID 54255612[3-(3-Hydroxyprop-1-ynyl)phenoxy]acetic acid tert-butyl esterAusbeute 68,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 178418476HCID 178418476, VerbindungKatalysator
HCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

The compound (1.00 g, 3.00 mmol) of Example 22-1 was dissolved in triethylamine (30 ml) under an atmosphere of nitrogen. Thereto were added propargyl alcohol (0.35 ml, 6.00 mmol), copper(I) iodide (6.00 mg, 30.0 μmol) and dichlorobis(triphenylphosphine)palladium (II) (42.0 mg, 60.0 μmol) and the mixture was stirred for 1 hour at 70° C. The mixture was cooled and thereto was added ethyl acetate. The mixture was washed with 10% aqueous citric acid solution, water, an aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution in the order and dried over sodium sulfate. The solvent was removed and purified with silica gel chromatography (hexane:ethyl acetate, 3:1–2:1) to give the subject compound as a yellow oil(537 mg, 68%).

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. washThe mixture was washed with 10% aqueous citric acid solution, water
  3. dry with materialan aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution in the order and dried over sodium sulfate
  4. customThe solvent was removed
  5. custompurified with silica gel chromatography (hexane:ethyl acetate, 3:1–2:1)

Quellen und Nachweise

ORD-Eintrag
ord-a2059c51137b4639919fccc3fccc2abe
Quelldatensatz
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07220773B2

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