Tetrahydrofuran → 5-(S)-methyl-7-(t-butyldimethylsilyloxy)-2-heptene

HRID 35722

Reaktionsgleichung

Reaktionsgleichung von HRID 35722
O1CC[CH2:3][CH2:2]1.C([Li])CCC.[CH3:11][C@H:12]([CH2:16][CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH2:13][CH:14]=O>[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)CC)C=CC=CC=1.O>[CH3:11][C@H:12]([CH2:16][CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH2:13][CH:14]=[CH:2][CH3:3]

Komponenten

6

Edukt 3

HCID 8028Tetrahydrofuran2×HCID 104438663-(R)-methyl-5-(t-butyldimethylsilyloxy)-1-pentanalHCID 178418339Butyllithium

Produkt 1

HCID 537803775-(S)-methyl-7-(t-butyldimethylsilyloxy)-2-heptene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)KatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

To a slurry of 80 g. (0.2155 m) of triphenyl-ethyl phosphonium bromide in 800 ml. of dry tetrahydrofuran cooled to 0° C. was added 165.7 ml. of 1.3M solution of n-butyl lithium (0.2155 m) in the same solvent. After 2 hours, 45 g. (0.196 m) 3-(R)-methyl-5-(t-butyldimethylsilyloxy)-1-pentanal in 200 ml. of dry tetrahydrofuran was added dropwise to the reaction mixture. The reaction was allowed to stir 2 hours at room temperature and was then poured into water and extracted with ether. The combined extracts were washed with water and a brine solution and dried over magnesium sulfate. Removal of the solvent in vacuo gave a yellow oil which, on distillation gave 37.4 g. of product, b.p. 74°-79° C./0.2-0.1 torr.

Aufarbeitung

  1. additionwas added 165.7 ml
  2. extractionextracted with ether
  3. washThe combined extracts were washed with water
  4. dry with materiala brine solution and dried over magnesium sulfate
  5. customRemoval of the solvent in vacuo
  6. customgave a yellow oil which
  7. distillationon distillation
  8. customgave 37.4 g

Quellen und Nachweise

ORD-Eintrag
ord-4c5114fdff2d45a59c871c8312f0440a
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04767743

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