1-(Bromomethyl)-3-ethylbenzene → 2-[2-[2-(3-Ethylphenyl)ethyl]-4-methylphenyl]-4,5-dihydro-4,4-dimethyloxazole

HRID 1871983

Reaktionsgleichung

Reaktionsgleichung von HRID 1871983
C([Li])CCC.[CH3:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[C:14]1[O:15][CH2:16][C:17]([CH3:20])([CH3:19])[N:18]=1.Br[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][CH3:30])[CH:24]=1>CCCC(C)C.O1CCCC1>[CH2:29]([C:25]1[CH:24]=[C:23]([CH2:22][CH2:6][C:7]2[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=2[C:14]2[O:15][CH2:16][C:17]([CH3:20])([CH3:19])[N:18]=2)[CH:28]=[CH:27][CH:26]=1)[CH3:30]

Komponenten

6

Edukt 3

HCID 220036561-(Bromomethyl)-3-ethylbenzeneHCID 221172732-[2,4-Dimethylphenyl]-4,5-dihydro-4,4-dimethyloxazoleHCID 178418339Butyllithium

Produkt 1

HCID 186897132-[2-[2-(3-Ethylphenyl)ethyl]-4-methylphenyl]-4,5-dihydro-4,4-dimethyloxazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 78922-MethylpentaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

n-Butyllithium (16.8 ml of a 2.5M solution in isohexane) was added dropwise to a stirred solution of the product of step (iii) (8.13 g) in dry tetrahydrofuran (ISOml) at 0° C. under nitrogen. After 1 hour, the product of step (ii) (8.0 g) in tetrahydrofliran (60 ml) was added. After 1 hour, the reaction was quenched with aqueous ammonium chloride and partitioned between ethyl acetate and water. The organic solution was dried (MgSO4) and evaporated. Purification was by chromatography eluting with 5% ethyl acetate in isohexane. Yield 4.93 g.

Aufarbeitung

  1. waitAfter 1 hour
  2. customthe reaction was quenched with aqueous ammonium chloride
  3. custompartitioned between ethyl acetate and water
  4. dry with materialThe organic solution was dried (MgSO4)
  5. customevaporated
  6. customPurification
  7. washeluting with 5% ethyl acetate in isohexane

Quellen und Nachweise

ORD-Eintrag
ord-6131338cbdc04d71916f960b0699ee4f
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06107297

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