Hexane → Ethyl 7-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]heptanoate

HRID 1584338

Reaktionsgleichung

Reaktionsgleichung von HRID 1584338
[Br-].[CH2:2]([O:4][C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:6])[CH3:3].[CH3:31]CCCCC.C([Li])CCC.[CH3:42][O:43][C:44]1[CH:45]=[C:46]([CH:49]=[CH:50][C:51]=1[O:52][CH2:53][C:54]1[N:55]=[C:56]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[O:57][C:58]=1[CH3:59])C=O>O1CCCC1.O>[CH3:42][O:43][C:44]1[CH:45]=[C:46]([CH2:31][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:5]([O:4][CH2:2][CH3:3])=[O:6])[CH:49]=[CH:50][C:51]=1[O:52][CH2:53][C:54]1[N:55]=[C:56]([C:60]2[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=2)[O:57][C:58]=1[CH3:59]

Komponenten

7

Edukt 4

HCID 8058HexaneHCID 10345271(5-Ethoxycarbonylpentyl)triphenylphosphonium bromideHCID 108297433-Methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzaldehydeHCID 178418339Butyllithium

Produkt 1

HCID 21224419Ethyl 7-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]heptanoateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of (5-ethoxycarbonylpentyl)triphenylphosphonium bromide (3.0 g) in tetrahydrofuran (THF) (70 ml) was added dropwise, in nitrogen streams at -30° C., a hexane solution of n-butyl lithium (1.6M, 3.9 ml). The mixture was stirred for 30 minutes at the same temperature, to which was added dropwise at -30° C. a solution of 3-methoxy-4-[5-methyl-2-phenyl-4-oxazolylmethoxy)benzaldehyde (1.0 g) in tetrahydrofuran (THF) (10 ml). The mixture was stirred for 4 hours at temperature ranging from 50 to 60° C. The reaction mixture was then poured into water, which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), followed by distilling off the solvent under reduced pressure. The residue was subjected to column chromatography on silica gel. From the fraction eluted with ethyl acetate-hexane (1:4), was obtained ethyl 7-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]heptanoate (9.7 g, 85%) as an oily product.

Aufarbeitung

  1. additionwas added dropwise, in nitrogen streams at -30° C.
  2. stirringThe mixture was stirred for 4 hours at temperature
  3. customranging from 50 to 60° C
  4. extractionwas subjected to extraction with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried (MgSO4)
  7. distillationby distilling off the solvent under reduced pressure
  8. washFrom the fraction eluted with ethyl acetate-hexane (1:4)

Quellen und Nachweise

ORD-Eintrag
ord-2c8c9a3a63424b8f92e3be6d51f1ccfe
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05932601

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