Benzoyl chloride → (3aR,6aS)-5-Formyl-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-yl benzoate

HRID 593395

Reaktionsgleichung

Reaktionsgleichung von HRID 593395
[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.CN(C1C=CC=CN=1)C.C(N(CC)CC)C.[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)Cl>[C:28]([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)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Komponenten

6

Edukt 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 72703147(3aR,6aS)-2-Hydroxy-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-5-carbaldehyde

Produkt 1

HCID 90019505(3aR,6aS)-5-Formyl-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-yl benzoate

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. Dimethylaminopyridine (23.5 mg, 0.19 mmol, 5 mol %) was added as a solid. Triethylamine (647.5 μl, 4.61 mmol, 1.2 eq.) and benzoyl chloride (534.5 μL, 4.61 mmol, 1.2 eq.) were added via syringe. The reaction mixture was stirred at r.t. for 36 h, filtered over basic alumina and the organic phase was concentrated to give the crude material. The material was purified by column chromatography eluting with petrol/EtOAc (3:1) to give the benzoyl acetal 55 (as an approximately 1.3:1 mixture of diasteroisomers, 706.7 mg, 71%) as pale yellow solid.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at r.t. for 36 h
  2. filtrationfiltered over basic alumina
  3. concentrationthe organic phase was concentrated
  4. customto give the crude material
  5. customThe material was purified by column chromatography
  6. washeluting with petrol/EtOAc (3:1)

Quellen und Nachweise

ORD-Eintrag
ord-ea547e51e76a4a729a318e3fdc178037
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242954B2

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