Cesium carbonate → HCID 68533499, Verbindung

HRID 2389323

Reaktionsgleichung

Reaktionsgleichung von HRID 2389323
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH2:9][CH2:10][CH2:11][OH:12].Cl[C@H:14]([CH3:19])[C:15]([O:17][CH3:18])=[O:16].C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C@@H:14]([CH3:19])[C:15]([O:17][CH3:18])=[O:16])=[CH:4][C:3]=1[CH2:9][CH2:10][CH2:11][OH:12]

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 149593Methyl 2-chloropropanoate, (R)-HCID 685363254-Fluoro-3-(3-hydroxypropyl)phenol

Produkt 1

HCID 68533499HCID 68533499, VerbindungAusbeute 66,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a mixture of 4-fluoro-3-(3-hydroxypropyl)phenol (1.5 g), methyl (2R)-2-chloropropanoate (1.30 g) in DMSO (7.5 mL) was added Cs2CO3 (3.45 g) at ambient temperature. The mixture was stirred at 60° C. for 3 hours. After cooling to ambient temperature, the reaction mixture was diluted with EtOAc (50 mL) and washed successively with water (30 mL) two times and brine (30 mL). The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo to give crude oil. The crude oil was purified by silica gel column chromatography (n-hexane:EtOAc=4:1-2:1) to give methyl(2S)-2-[4-fluoro-3-(3-hydroxypropyl)phenoxy]propanoate (1.51 g) as a colorless oil.

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature
  2. washwashed successively with water (30 mL) two times and brine (30 mL)
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give crude oil
  7. customThe crude oil was purified by silica gel column chromatography (n-hexane:EtOAc=4:1-2:1)

Quellen und Nachweise

ORD-Eintrag
ord-6c2c0f1bedca4ae4af36eb8e4e219608
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08273745B2

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