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

HRID 1250111Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1250111
[CH2:1]([OH:4])[C:2]#[CH:3].[C:5]([O:9][C:10](=[O:20])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15](Br)[CH:14]=1)([CH3:8])([CH3:7])[CH3:6].[Cl-].[NH4+]>N1CCCC1.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>[C:5]([O:9][C:10](=[O:20])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:3]#[C:2][CH2:1][OH:4])[CH:14]=1)([CH3:8])([CH3:7])[CH3:6]

Komponenten

6

Edukt 3

HCID 7859Propargyl alcoholHCID 25517Ammonium ChlorideHCID 20577391tert-Butyl 2-(3-bromophenoxy)acetate

Produkt 1

HCID 54255612[3-(3-Hydroxyprop-1-ynyl)phenoxy]acetic acid tert-butyl esterAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 31268PyrrolidineLösungsmittel

Reaktionsbedingungen

Temperatur
77.5 °C

Versuchsvorschrift

Tetrakis(triphenylphosphine)palladium(0) (0.66 g, 0.57 mmol) and propargyl alcohol (1.34 mL, 22.97 mmol) were added to a solution of (3-bromophenoxy) acetic acid tert-butyl ester (3.3 g, 11.49 mmol) in pyrrolidine (35 mL) under an argon atmosphere at room temperature. The mixture was heated at 75-80° C. for 2.5 hours. Excess saturated ammonium chloride was added and the mixture was extracted with diethyl ether. The extract was washed with brine, dried over sodium sulfate, and concentrated to dryness. Purification by flash chromatography, eluting with hexane/ethyl acetate, gave [3-(3-hydroxyprop-1-ynyl)phenoxy]acetic acid tert-butyl ester as a pale yellow oil (1.93 g, 64%).

Aufarbeitung

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe extract was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness
  5. customPurification by flash chromatography
  6. washeluting with hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-00bf84f5715d49e0afb0ce73e180434c
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06335459B1

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