Pyridine → ((2S,4R)-4,5-diacetoxy-4-methyl-tetrahydrofuran-2-yl)methyl benzoate

HRID 409011

Reaktionsgleichung

Reaktionsgleichung von HRID 409011
[C:1]([O:9][CH2:10][C@H:11]1[O:18][CH:17]2[C@:13]([CH3:21])([O:14][C:15]([CH3:20])(C)[O:16]2)[CH2:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][C:23]([O:25]C(C)=O)=[O:24].N1C=CC=CC=1.[CH2-]C(C)=O>C(O)(=O)C.C(OCC)(=O)C.CN(C1C=CN=CC=1)C>[C:1]([O:9][CH2:10][C@@H:11]1[CH2:12][C@:13]([O:25][C:23](=[O:24])[CH3:22])([CH3:21])[CH:17]([O:16][C:15](=[O:14])[CH3:20])[O:18]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

8

Edukt 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 66778757((5S,6aR)-2,2,6a-trimethyl-dihydro-5H-furo[3,2-d][1,3]dioxol-5-yl)methyl benzoateHCID 178477758HCID 178477758, Verbindung

Produkt 1

HCID 66779482((2S,4R)-4,5-diacetoxy-4-methyl-tetrahydrofuran-2-yl)methyl benzoateAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 3.8 g of ((5S,6aR)-2,2,6a-trimethyl-dihydro-5H-furo[3,2-d][1,3]dioxol-5-yl)methyl benzoate (from step 9) in 25 mL of 70% acetic acid was heated to 70° C. for 48 h. The reaction mixture was diluted with ethyl acetate and washed with water and saturated NaHCO3. The organic layers were dried over anhydrous Na2SO4, filtered and concentrated. Crude diol obtained was aceylated using Ac2O (0.03373 mol, 3.18 mL) and 20 mL of anhydrous pyridine with catalytic amount of DMAP (5 mol %). The progress of the reaction was monitored by TLC. Pyridine was removed under vacuum and the residue was diluted with ethyl acetate and was washed with 1N HCl and saturated NaHCO3. The organic layers were dried over anhydrous Na2SO4, filtered and concentrated. Purified by column chromatography to give 3.3 g of the title compound (88% yield) and 0.55 g of starting material acetonide was recovered.

Aufarbeitung

  1. washwashed with water and saturated NaHCO3
  2. dry with materialThe organic layers were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customCrude diol obtained
  6. customPyridine was removed under vacuum
  7. additionthe residue was diluted with ethyl acetate
  8. washwas washed with 1N HCl and saturated NaHCO3
  9. dry with materialThe organic layers were dried over anhydrous Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customPurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c11def04f66b48289510920811fe42b7
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759318B2

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