Oxiranemethanol, 3-[(phenylmethoxy)methyl]- → 3-Allyl-4-(benzyloxy)-3-hydroxy-1-butanol

HRID 400233

Reaktionsgleichung

Reaktionsgleichung von HRID 400233
[CH2:1]([O:8][CH2:9][CH:10]1[O:14][CH:11]1[CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([Mg]Cl)[CH:16]=[CH2:17]>O1CCCC1>[CH2:17]([C:10]([OH:14])([CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:11][CH2:12][OH:13])[CH:16]=[CH2:15]

Komponenten

4

Edukt 2

HCID 3934498Oxiranemethanol, 3-[(phenylmethoxy)methyl]-HCID 178418473HCID 178418473, Verbindung

Produkt 1

HCID 189441063-Allyl-4-(benzyloxy)-3-hydroxy-1-butanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-40 °C

Versuchsvorschrift

A solution of 4-benzyloxy-2,3-epoxy-1-butanol (6.28 g, 32.37 mmol) in anhydrous tetrahydrofuran (75 mL) was added dropwise at -40° C. over a period of 45 minutes, to a 2M solution of allyl magnesium chloride (48.5 mL, 97 mmol) and tetrahydrofuran (50 mL). The solution was stirred at -40° C. for 1 hour, warmed to 0° C. and quenched by addition of aqueous ammonium chloride solution. The tetrahydrofuran layer was separated and the aqueous layer was extracted with ethyl acetate (three times). The combined organic extract was dried (magnesium sulfate), filtered and concentrated to obtain a mixture of compounds A and B.

Aufarbeitung

  1. temperaturewarmed to 0° C.
  2. customquenched by addition of aqueous ammonium chloride solution
  3. customThe tetrahydrofuran layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (three times)
  5. extractionThe combined organic extract
  6. dry with materialwas dried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto obtain

Quellen und Nachweise

ORD-Eintrag
ord-757e5a1c8b554ab7918a14250606dd48
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05827868

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