(5-Carboxypentyl)triphenylphosphanium bromide → HCID 53684295, Verbindung

HRID 367306

Reaktionsgleichung

Reaktionsgleichung von HRID 367306
CC(C)([O-])C.[K+].[Br-].[C:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:10])=[O:9].[C:35]([C:39]1[C:44]2[CH2:45][C:46](C=O)([CH3:48])[O:47][C:43]=2[CH:42]=[C:41]([C:51]([CH3:54])([CH3:53])[CH3:52])[C:40]=1[O:55][Si](C)(C)C)([CH3:38])([CH3:37])[CH3:36]>C1COCC1>[C:35]([C:39]1[C:44]2[CH2:45][C:46]([CH:15]=[CH:14][CH2:13][CH2:12][CH2:11][C:8]([OH:10])=[O:9])([CH3:48])[O:47][C:43]=2[CH:42]=[C:41]([C:51]([CH3:54])([CH3:53])[CH3:52])[C:40]=1[OH:55])([CH3:38])([CH3:37])[CH3:36]

Komponenten

5

Edukt 3

HCID 2779280(5-Carboxypentyl)triphenylphosphanium bromideHCID 23288036HCID 23288036, VerbindungHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 53684295HCID 53684295, VerbindungAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

Under a nitrogen atmosphere, a solution of 0.92 g of potassium t-butoxide in 10 ml of THF was added dropwise to a suspension of 0.46 g of 5-carboxypentyltriphenylphosphonium bromide in 5 ml of THF at 0° C., and the mixture was stirred for 30 minutes. To the reaction solution was added dropwise a solution of 4,6-di-t-butyl-2-formyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran synthesized in Example 72-2) in 10 ml of THF, and the mixture was stirred overnight while slowly warming to room temperature. The reaction solution was extracted with water and diethyl ether, and the combined aqueous layers were acidified with concentrated hydrochloric acid and extracted with diethyl ether. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography eluting with n-hexane containing 50% ethyl acetate to give 0.22 g of 6-(4,6-di-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran-2-yl)-5-hexenoic acid as a colorless viscous liquid (yield 43%).

Aufarbeitung

  1. stirringthe mixture was stirred overnight
  2. extractionThe reaction solution was extracted with water and diethyl ether
  3. extractionextracted with diethyl ether
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with n-hexane containing 50% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-9301289ae4924d06bc13c186d034667f
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06133279

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