Benzyl Alcohol → (3aR,6aS)-2-(Benzyloxy)-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-5-carbaldehyde

HRID 593396Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 593396
[OH:1][CH:2]1[O:6][C@H:5]2[CH2:7][C:8]([CH:10]=[O:11])=[CH:9][C@H:4]2[CH2:3]1.[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[O-]S([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[CH2:12]([O:1][CH:2]1[O:6][C@H:5]2[CH2:7][C:8]([CH:10]=[O:11])=[CH:9][C@H:4]2[CH2:3]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

5

Edukt 3

HCID 244Benzyl AlcoholHCID 24083Sulfuric acid magnesium salt (1:1)HCID 72703147(3aR,6aS)-2-Hydroxy-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-5-carbaldehyde

Produkt 1

HCID 118117763(3aR,6aS)-2-(Benzyloxy)-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-5-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Purified lactol 7 (591.5 mg, 3.84 mmol, 1 eq.), was dissolved in CH2Cl2 (7 ml) and stirred at r.t. Benzyl alcohol (794.1 μL, 7.68 mmol, 2 eq.) was added via syringe and amberlyst 15 (56.5 mg) and MgSO4 (1.16 g) were added as solids. The reaction mixture was stirred at r.t. for 36 h. The reaction mixture was filtered through a sinter funnel and the solids washed with CH2Cl2 (2×10 ml). The filtrate was concentrated under reduced pressure to give the crude material which was purified by column chromatography eluting with petrol/EtOAc (9:1) to give the benzyl acetal 56 (as an approximately 1.5:1 mixture of diasteroisomers, 657.8 mg, 70%) as pale yellow oil.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at r.t. for 36 h
  2. filtrationThe reaction mixture was filtered through a sinter funnel
  3. washthe solids washed with CH2Cl2 (2×10 ml)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto give the crude material which
  6. customwas purified by column chromatography
  7. washeluting with petrol/EtOAc (9:1)

Quellen und Nachweise

ORD-Eintrag
ord-42e72c3589d84cb0b8d84392dc20ca15
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242954B2

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