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2,5-Dichlorophenol → [3-(2,5-Dichlorophenoxy)pentyl]methylcarbamic acid, 1,1-dimethylethyl ester

HRID 2183834
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2183834
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[OH:9].O[CH:11]([CH2:23][CH3:24])[CH2:12][CH2:13][N:14]([CH3:22])[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.O>[CH3:20][C:17]([O:16][C:15](=[O:21])[N:14]([CH2:13][CH2:12][CH:11]([O:9][C:3]1[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=1[Cl:1])[CH2:23][CH3:24])[CH3:22])([CH3:18])[CH3:19]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 662,5-DichlorophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 857904251,1-Dimethylethyl (3-hydroxypentyl)methylcarbamate

Produkt 1

HCID 86587540[3-(2,5-Dichlorophenoxy)pentyl]methylcarbamic acid, 1,1-dimethylethyl esterAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2,5-Dichlorophenol (325 mg, 2.00 mmol) and (3-hydroxypentyl)methylcarbamic acid, 1,1-dimethylethyl ester (217 mg, 1.00 mmol) were dissolved in tetrahydrofuran (10 ml). To the resulting solution was added triphenylphosphine (393 mg, 1.50 mmol) and then diethyl azodicarboxylate (0.240 ml, 1.52 mmol). The solution was then allowed to stir at room temperature under nitrogen for 24 h. The mixture was then poured into water and extracted three times with diethyl ether. The combined organic fractions were washed with 1N sodium hydroxide solution twice and then brine and dried over magnesium sulfate. The solvent was evaporated and the residue eluted down a flash chromatography column using 10% ethyl acetate/isohexane as eluent to give 180 mg (50%) of the title compound as an oil.

Aufarbeitung

  1. extractionextracted three times with diethyl ether
  2. washThe combined organic fractions were washed with 1N sodium hydroxide solution twice
  3. dry with materialbrine and dried over magnesium sulfate
  4. customThe solvent was evaporated
  5. washthe residue eluted down a flash chromatography column

Quellen und Nachweise

ORD-Eintrag
ord-b503292cd0c642abb80dbe4e4a3af87c
Quelldatensatz
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06900243B2

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