Tetrahydrofuran → Ethyl 2-[(1,1'-biphenyl)-4-yl]-2-hydroxypropionate

HRID 1385020Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1385020
[C:1]1([C:7]2[CH:19]=[CH:18][C:10]([C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:12])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:20]1COCC1.C[Mg]I.[NH4+].[Cl-]>CCOCC>[C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:19]=[CH:18][C:10]([C:11]([OH:12])([CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][CH:8]=1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 80389Ethyl 4-phenylbenzoylformateHCID 178418373HCID 178418373, Verbindung

Produkt 1

HCID 21184093Ethyl 2-[(1,1'-biphenyl)-4-yl]-2-hydroxypropionate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
-25 °C

Versuchsvorschrift

To a flame dried 500 mL flask flushed with N2, was added 24 g (100 mmol) of ethyl 4-phenylbenzoylformate and 300 mL of anhydrous THF. The solution was cooled with stirring to −25° C. and 37 mL (110 mmol) of a 3.0M solution of methylmagnesium iodide was added at a rate to maintain the reaction temperature below −10° C. The reaction progress was monitored by TLC and upon disappearance of starting material, 100 mL of saturated NH4Cl solution and 200 mL of ether were added. The organic layer was separated and washed with 2×50 mL of brine, dried (MgSO4) and concentrated leaving racemic ethyl 2-[(1,1′-biphenyl)4-yl]-2-hydroxypropionate as an oil.

Aufarbeitung

  1. customTo a flame dried 500 mL flask
  2. customflushed with N2
  3. temperatureThe solution was cooled
  4. temperatureto maintain the reaction temperature below −10° C
  5. additionwere added
  6. customThe organic layer was separated
  7. washwashed with 2×50 mL of brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0d57d9efaa564cc4a7b04a05ed1f2169
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06262073B1

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