Benzoyl chloride → (6-Hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

HRID 2191009

Reaktionsgleichung

Reaktionsgleichung von HRID 2191009
[CH3:1][C:2]1([CH3:13])[O:9][C@@H:8]2[C@@H:4]([C@@H:5]([OH:12])[C@@H:6]([CH2:10][OH:11])[O:7]2)[O:3]1.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)Cl.O>[OH:12][CH:5]1[CH:4]2[CH:8]([O:9][C:2]([CH3:13])([CH3:1])[O:3]2)[O:7][CH:6]1[CH2:10][O:11][C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

5

Edukt 2

HCID 7412Benzoyl chlorideHCID 883381,2-O-isopropylidene-alpha-D-xylofuranose

Produkt 1

HCID 228800(6-Hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoateAusbeute 74,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

1,2-O-Isopropylidene-α-D-xylofuranose (Aldrich, 20 g, 100 mmol) in CH2Cl2 (300 mL) and TEA (44 mL, 310 mmol) was cooled to 0° C. The solution was treated with benzoyl chloride (12.8 mL, 110 mmol) in CH2Cl2 (10 mL) dropwise and stirred for 2 h. The solution was diluted with H2O (30 mL) and washed with saturated NaHCO3 (2×30 mL). The solution was dried over MgSO4, filtered and concentrated in vacuo. The residue was treated to flash column chromatography (SiO2, 4×20 cm, 0-100% EtOAc-hexanes gradient) to afford compound 9.2 (22.0 g, 71% yield). (Taken from: Johnson, C. R.; Bhumralkar, D. R. Nucleosides & Nucleotides 1995, 14, 185.)

Aufarbeitung

  1. washwashed with saturated NaHCO3 (2×30 mL)
  2. dry with materialThe solution was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. additionThe residue was treated to flash column chromatography (SiO2, 4×20 cm, 0-100% EtOAc-hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-97161bbd8239407b97df770691c18309
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324179B2

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