Benzyl Alcohol → Benzyl oxolan-3-ylcarbamate

HRID 2042961Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2042961
[O:1]1[CH2:5][CH2:4][CH:3](C(O)=O)[CH2:2]1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:16])C=CC=CC=1.[CH2:26]([OH:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C([N:36]([CH2:39]C)CC)C>O1CCOCC1>[CH2:26]([O:33][C:39]([NH:36][CH:3]1[CH2:4][CH2:5][O:1][CH2:2]1)=[O:16])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Komponenten

6

Edukt 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 4661317(R)-Tetrahydro-3-furoic acid

Produkt 1

HCID 21864525Benzyl oxolan-3-ylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

12.36 ml of tetrahydrofuran-3-carboxylic acid and 27.84 ml of diphenylphosphorylazide in 500 ml of dioxane are combined with 41.91 g of benzyl alcohol and 35.81 ml of triethylamine. The reaction mixture is heated to 100° C. for about seven hours. After cooling to ambient temperature, the reaction mixture is evaporated down using the rotary evaporator. The residue is taken up in 500 ml of methylene chloride and washed twice with 100 ml of 1 N sodium hydroxide solution. The organic phase is dried over magnesium sulfate and evaporated down. The crude product is purified by chromatography over a silica gel column with cyclohexane/ethyl acetate (3:1 to 1:2) as eluant. Yield: 15.60 g (55% of theory); mass spectrum (ESI−): m/z=220 [M−H]−; Rf value: 0.78 (silica gel, methylene chloride/methanol=9:1).

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature
  2. customthe reaction mixture is evaporated down
  3. customthe rotary evaporator
  4. washwashed twice with 100 ml of 1 N sodium hydroxide solution
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. customevaporated down
  7. customThe crude product is purified by chromatography over a silica gel column with cyclohexane/ethyl acetate (3:1 to 1:2) as eluant

Quellen und Nachweise

ORD-Eintrag
ord-aa0c41d6e8cf434184a9d8e77e5502b0
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586608B2

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