Hydrochloric Acid → HCID 69290984, Verbindung

HRID 1247339Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1247339
[F:1][C:2]1[CH:3]=[C:4]([O:9][CH3:10])[CH:5]=[C:6]([F:8])[CH:7]=1.CN(C)[CH2:13][CH2:14]N(C)CCN(C)C.C([Li])CCC.C([C:30](=[O:34])[C:31]([O-:33])=[O:32])C.Cl>C1COCC1.O>[CH2:13]([O:33][C:31](=[O:32])[CH:30]([C:7]1[C:2]([F:1])=[CH:3][C:4]([O:9][CH3:10])=[CH:5][C:6]=1[F:8])[OH:34])[CH3:14]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 18196PentamethyldiethylenetriamineHCID 27245183,5-DifluoroanisoleHCID 35932772-KetobutyrateHCID 178418339Butyllithium

Produkt 1

HCID 69290984HCID 69290984, VerbindungAusbeute 38,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3,5-difluoroanisole (20 g) in THF (200 ml) was added pentamethyldiethylenetriamine (24.05 g). The mixture was cooled to −75° C. n-butyllithium (85 ml, 1.6 M in hexane) was added in such a way that the temperature did not exceed −67° C. The mixture was stirred for 2 h. Ethylglyoxalate (55.5 g, 50% in toluene) was added and the mixture was stirred for a further 2 h. Afterwards, the mixture was allowed to warm up to rt. Water was added and the mixture was made acidic (pH 3) with 25% HCl. The mixture was extracted with EtOAc. The organic phase was washed with 0.5 N HCl, dried, filtered and concentrated. The product was purified by flash chromatography (SiO2, cyclohexane/EtOAc 7:1) to give (RS)-(2,6-difluoro-4-methoxy-phenyl)-hydroxy-acetic acid ethyl ester (13.09 g). Colorless oil. MS 246.1 ([M]+)

Aufarbeitung

  1. additionwas added in such a way that the temperature
  2. customdid not exceed −67° C
  3. stirringthe mixture was stirred for a further 2 h
  4. extractionThe mixture was extracted with EtOAc
  5. washThe organic phase was washed with 0.5 N HCl
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe product was purified by flash chromatography (SiO2, cyclohexane/EtOAc 7:1)

Quellen und Nachweise

ORD-Eintrag
ord-b7e68f7765b3486f971a9705afe3e3a0
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129238B2

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