Thionyl Chloride → 5-(benzyloxy)-2-(chloromethyl)-4H-pyran-4-one

HRID 1056895Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1056895
[CH2:1]([O:8][C:9]1[C:10](=[O:17])[CH:11]=[C:12]([CH2:15]O)[O:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=S(Cl)[Cl:20]>CCOCC>[CH2:1]([O:8][C:9]1[C:10](=[O:17])[CH:11]=[C:12]([CH2:15][Cl:20])[O:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 9015985-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one

Produkt 1

HCID 37033215-(benzyloxy)-2-(chloromethyl)-4H-pyran-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a suspension of 5-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one (18.5 g, 80 mmol) in Et2O (130 mL) was added SOCl2 (18 mL, 1 10 mmol) at r.t. and the mixture was stirred for 1 h. The reaction mixture was poured onto ice-water and more Et20 was added. Then the Et20 phase was collected and water phase was extracted by Et20 twice, the combined Et20 layer was washed with brine, dried over Na2S04, and concentrated. The residue was purified by silica gel chromatography to give 5-(benzyloxy)-2-(chloromethyl)-4H-pyran-4-one 1HNMR (DMSO, 400 MHZ) δ 8.27 (s, 1H), 7.32-7.41 (m, 5H)S 6.55 (s, 1H), 4.92 (s, 2H), 4.65 (s, 2H). MS (M+H)+250.1/252.1.

Aufarbeitung

  1. additionThe reaction mixture was poured onto ice-water and more Et20
  2. additionwas added
  3. customThen the Et20 phase was collected
  4. extractionwater phase was extracted by Et20 twice
  5. washthe combined Et20 layer was washed with brine
  6. customdried over Na2S04
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-21b3fb542d7e4168bb1f8138517cca5b
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09399651B2

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