Benzyl Bromide → (1R,2S,4R,5S)-5-(Benzyloxy)bicyclo[2.2.1]heptan-2-ol

HRID 1158069Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1158069
[C@@H:1]12[CH2:8][C@@H:4]([C@@H:5]([OH:7])[CH2:6]1)[CH2:3][C@@H:2]2[OH:9].C1OCCOCCOCCOCCOC1.O1CCCC1.[OH-].[Na+].Br[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[CH2:33]([O:7][C@H:5]1[CH2:6][C@H:1]2[CH2:8][C@@H:4]1[CH2:3][C@@H:2]2[OH:9])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Komponenten

6

Edukt 5

HCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 3633615-Crown-5HCID 9989289(1R,2S,4R,5S)-Bicyclo[2.2.1]heptane-2,5-diol

Produkt 1

HCID 10036335(1R,2S,4R,5S)-5-(Benzyloxy)bicyclo[2.2.1]heptan-2-ol

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

To a stirred solution of (1R,2S,4R,5S)-bicyclo[2.2.1]-heptane-2,5-diol (1.15 g, 8.97 mmol) and 15-crown-5 (0.054 mL, 0.269 mmol) in tetrahydrofuran (30.0 mL, 8.97 mmol) were added at 10° C. (ice/water bath) finely ground sodium hydroxide (2.15 g, 53.8 mmol) and 1-(bromomethyl)benzene (1.07 mL, 8.97 mmol). After stirring at 10° C. for 3 h, the mixture was stirred at ambient temperature overnight. The mixture was partitioned between EtOAc and water, and the organic portions were washed with brine, and conc. in vacuo. The crude product was purified by flash column chromatography (0 to 80% of ethyl acetate in hexanes). The title compound was obtained as a colorless oil.

Aufarbeitung

  1. stirringthe mixture was stirred at ambient temperature overnight
  2. customThe mixture was partitioned between EtOAc and water
  3. washthe organic portions were washed with brine
  4. customThe crude product was purified by flash column chromatography (0 to 80% of ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-e38b69096b4b49c1b57286c89b0be024
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807700B2

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