Triphenylmethane → (S)-4-benzyl-3-(3,4-dichlorophenyl)acetyl-2-oxazolidinone

HRID 429467Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 429467
C1[N:6](CC2C=CC=CC=2)[C:4](=[O:5])[O:3]C1.C1([CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=CC=CC=2)C=CC=CC=1.C([Li])CCC.CC(C)(C)C(O[C:43](=[O:53])[CH2:44][C:45]1[CH:50]=[CH:49][C:48]([Cl:51])=[C:47]([Cl:52])[CH:46]=1)=O.[Li][C@H]1COC(=O)N1CC1C=CC=CC=1>C(OCC)(=O)C.CCCCCC.O1CCCC1>[CH2:20]([C@H:21]1[CH2:26][O:5][C:4](=[O:3])[N:6]1[C:43](=[O:53])[CH2:44][C:45]1[CH:50]=[CH:49][C:48]([Cl:51])=[C:47]([Cl:52])[CH:46]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Komponenten

8

Edukt 5

HCID 10614TriphenylmethaneHCID 104875283-Benzyl-1,3-oxazolidin-2-oneHCID 539526903,4-Dichlorophenylacetic acid trimethylacetyl esterHCID 178418339ButyllithiumHCID 178506844HCID 178506844, Verbindung

Produkt 1

HCID 69777551(S)-4-benzyl-3-(3,4-dichlorophenyl)acetyl-2-oxazolidinone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-40 °C

Versuchsvorschrift

Alternately, combine (S)-benzyl-2-oxazolidinone (25 g, 140 mmol) and tetrahydrofuran (250 ml). Add triphenylmethane (30 mg) as an indicator. Cool to about −40° C. Add n-butyl lithium (about 56 ml, 1 M in hexane, 140 mmol) until an orange color persists. After 30 minutes, cool in a dry-ice/acetone bath the a solution of 3,4-dichlorophenylacetic acid trimethylacetyl ester as obtained in Preparation 3 and add by cannula the solution of lithio (S)-benzyl-2-oxazolidinone obtained above. When the addition is complete warm to ambient temperature. After 18 hours, partition the reaction mixture between diethyl ether and a saturated aqueous sodium bicarbonate solution. Separate the layers and dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially is with 5% ethyl acetate/hexane and 10% ethyl acetate/hexane to give (S)-4-benzyl-3-(3,4-dichlorophenyl)acetyl-2-oxazolidinone.

Aufarbeitung

  1. customas obtained in Preparation 3
  2. customobtained above
  3. additionWhen the addition
  4. temperatureis complete warm to ambient temperature
  5. waitAfter 18 hours
  6. custompartition the reaction mixture between diethyl ether
  7. customSeparate the layers
  8. dry with materialdry the organic layer over MgSO4
  9. filtrationfilter
  10. customevaporate in vacuo
  11. customto give a residue

Quellen und Nachweise

ORD-Eintrag
ord-7e7c19cafc2d46ac9a413a7261ea5a7d
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06316445B1

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