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Acetic Acid → (3R,4S,7S) 3,7-dibenzyloxy-4-vinyldodeca-5-enecarboaldehyde

HRID 248605
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 248605
[CH2:1]([O:8][C@@H:9]([C@@H:16]([CH:33]=[CH2:34])[CH:17]=[CH:18][C@@H:19](OCC1C=CC=CC=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:10][CH:11](OC)OC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:35](=[O:38])(O)[O-].[Na+].[C:40]([OH:43])(=O)[CH3:41]>O1CCCC1>[CH2:1]([O:8][C@@H:9]([C@@H:16]([CH:33]=[CH2:34])[CH:17]=[CH:18][C@@H:19]([O:43][CH2:40][C:41]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:10][CH2:11][CH:35]=[O:38])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 67862608(3 R,4S,7S) 3,7-dibenzyloxy-4-vinyl-1,1-dimethoxydodeca-5-ene

Produkt 1

HCID 86746684(3R,4S,7S) 3,7-dibenzyloxy-4-vinyldodeca-5-enecarboaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

While stirring, 776 mg (1.67 mM) of (3R,4S,7S) 3,7-dibenzyloxy-4-vinyl-1,1-dimethoxydodeca-5-ene [8] described above was heated in a mixture of 13 ml of 80% acetic acid and 2 ml of tetrahydrofuran at 40° C. for 5 hours. Completion of the reaction was confimred by thin layer chromatography. Then, the reaction solution was poured into saturated sodium bicarbonate aqueous solution. The mixture was extracted 3 times with a solvent mixture of diethyl ether : hexane=7:3. The extracts were combined and washed sequentially with saturated sodium bicarbonate aqueous solution and saturated sodium chloride aqueous solution After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to give 701 mg (1.67 mM) of (3R,4S,7S) 3,7-dibenzyloxy-4-vinyldodeca-5-enecarboaldehyde [9]. Yield, 100%.

Aufarbeitung

  1. extractionThe mixture was extracted 3 times
  2. additionwith a solvent mixture of diethyl ether
  3. washwashed sequentially with saturated sodium bicarbonate aqueous solution and saturated sodium chloride aqueous solution
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-837aab2eb68c4cf4888dd2839968ae46
Quelldatensatz
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05210201

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