Nitrogen → 2-(5-Chloromethyl-furan-2-yl)-2-methyl-[1,3]dioxolane

HRID 1189425

Reaktionsgleichung

Reaktionsgleichung von HRID 1189425
N#N.[CH3:3][C:4]1([C:9]2[O:13][C:12]([CH2:14]O)=[CH:11][CH:10]=2)[O:8][CH2:7][CH2:6][O:5]1.CCN(CC)CC.S([Cl:27])(C)(=O)=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:27][CH2:14][C:12]1[O:13][C:9]([C:4]2([CH3:3])[O:8][CH2:7][CH2:6][O:5]2)=[CH:10][CH:11]=1

Komponenten

7

Edukt 4

HCID 947NitrogenHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66929165[5-(2-Methyl-[1,3]dioxolan-2-yl)-furan-2-yl]-methanol

Produkt 1

HCID 669289652-(5-Chloromethyl-furan-2-yl)-2-methyl-[1,3]dioxolane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [5-(2-methyl-[1,3]dioxolan-2-yl)-furan-2-yl]-methanol (3.50 g, 19.00 mmol) in dry CH2Cl2 (35.0 mL) was treated at 0° C. with Et3N (3.44 mL, 22.80 mmol) followed by DMAP (232 mg, 1.90 mmol) and Ms-Cl (1.77 mL, 22.80 mmol). After stirring at rt for 2 h, the reaction mixture was quenched with water (40 mL), extracted with CH2Cl2 (40 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced. Purification of the residue by FC (8:2:0.1 hept-EA-Et3N) gave the title compound as a yellow oil: TLC: rf (4:1 hept-EA)=0.35.

Aufarbeitung

  1. customthe reaction mixture was quenched with water (40 mL)
  2. extractionextracted with CH2Cl2 (40 mL)
  3. dry with materialextracts were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed
  6. customPurification of the residue by FC (8:2:0.1 hept-EA-Et3N)

Quellen und Nachweise

ORD-Eintrag
ord-cbc8413340ef464db9f0c75fcde16885
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08674111B2

Verknüpfte Notizen

Wird geladen…