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Triphenylphosphine → 2-Hexyloxy-3-[4-(2-{4-methanesulfonyloxyphenyl}-ethoxy)phenyl]propanoic acid methyl ester

HRID 987243
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 987243
[CH3:1][O:2][C:3](=[O:20])[CH:4]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[CH3:21][S:22]([O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33]O)=[CH:28][CH:27]=1)(=[O:24])=[O:23].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH3:1][O:2][C:3](=[O:20])[CH:4]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:33][CH2:32][C:29]2[CH:28]=[CH:27][C:26]([O:25][S:22]([CH3:21])(=[O:23])=[O:24])=[CH:31][CH:30]=2)=[CH:8][CH:7]=1
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Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 229887694-(2-Hydroxyethyl)phenyl methanesulfonateHCID 572290252-Hexyloxy-3-(4-hydroxyphenyl)propanoic acid methyl ester

Produkt 1

HCID 569752562-Hexyloxy-3-[4-(2-{4-methanesulfonyloxyphenyl}-ethoxy)phenyl]propanoic acid methyl esterAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

2-Hexyloxy-3-(4-hydroxyphenyl)propanoic acid methyl ester (0.33 g, 1.19 mmole) and 2-(4-methanesulfonyloxyphenyl)ethanol (0.2578 g; 1.19 mmole) was dissolved in dichloromethane (5 ml) under argon. Azodicarbonyl dipiperidine (0.451 g; 1.789 mmole) was added followed by addition of triphenylphosphine (0.375 g; 1.423 mmole). The reaction mixture was stirred at room temperature and after 2 hours more dichloromethane (2 ml) was added. The reaction mixture was stirred for another 18 hours and then filtered. The filtrate was washed with water, sodium hydrogen carbonate solution, diluted potassium hydrogen sulfate solution and brine, dried with sodium sulfate and evaporated. Chromatography of the residue on silica gel using heptane:ethyl acetat (2:1 to 1:1) as eluant gave 0.381 g (67% yield) of 2-hexyloxy-3-[4-(2-{4-methanesulfonyloxyphenyl}-ethoxy)phenyl]propanoic acid methyl ester.

Aufarbeitung

  1. additionwas added
  2. filtrationfiltered
  3. washThe filtrate was washed with water, sodium hydrogen carbonate solution, diluted potassium hydrogen sulfate solution and brine
  4. dry with materialdried with sodium sulfate
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-596c8c7f5368429bb572668e2b0555f0
Quelldatensatz
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06630600B1

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