Benzyl Bromide → 2-[3,4-Dimethoxy-2-phenylmethylphenyl]-4,5-dihydro-4,4-dimethyloxazole

HRID 2414007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2414007
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[O:12][CH2:13][C:14]([CH3:17])([CH3:16])[N:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C([Li])CCC.[C:23]1([CH2:29]Br)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1>[CH3:1][O:2][C:3]1[C:4]([CH2:29][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:5]([C:11]2[O:12][CH2:13][C:14]([CH3:17])([CH3:16])[N:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 27791682-(3,4-Dimethoxyphenyl)-4,4-dimethyl-2-oxazolineHCID 178418339Butyllithium

Produkt 1

HCID 212762762-[3,4-Dimethoxy-2-phenylmethylphenyl]-4,5-dihydro-4,4-dimethyloxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2-[3,4-Dimethoxyphenyl]-4,5-dihydro 4,4-dimethyloxazole (15 g) in dry tetrahydrofuran (100 ml) under a nitrogen atmosphere was cooled to -45° in a chlorobenzene/dry ice bath. Butyl lithium (45.9 ml 1.6 M solution) was added dropwise and the mixture stirred at -45° for 2 hours. Phenylmethyl bromide (38 ml) was then added dropwise and the mixture allowed to stir at 20° for 16 hours. The mixture was quenched with brine and the aqueous phase extracted with ether. The organic phase was separated, dried over magnesium sulphate, filtered and evaporated to leave a solid. Purification by flash chromatography (30% ether/40/60 petrol) gave the title compound as a colourless solid (10.58 g); mp 81°-82°.

Aufarbeitung

  1. stirringto stir at 20° for 16 hours
  2. customThe mixture was quenched with brine
  3. extractionthe aqueous phase extracted with ether
  4. customThe organic phase was separated
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customto leave a solid
  9. customPurification by flash chromatography (30% ether/40/60 petrol)

Quellen und Nachweise

ORD-Eintrag
ord-af121901f242409bb812c38a5d0a45db
Quelldatensatz
uspto-grants-1988_01
Patentnummer
US04720586

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