Dimethyl Sulfoxide → 6-((benzyloxy)methyl)dihydro-2H-pyran-3(4H)-one

HRID 1045405

Reaktionsgleichung

Reaktionsgleichung von HRID 1045405
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([O:18][CH2:19][CH:20]1[O:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C.[NH4+].[Cl-]>ClCCl>[CH2:11]([O:18][CH2:19][CH:20]1[O:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Komponenten

7

Edukt 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 580637066-(benzyloxymethyl)tetrahydro-2H-pyran-3-ol

Produkt 1

HCID 580636326-((benzyloxy)methyl)dihydro-2H-pyran-3(4H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

DMSO (1.15 mL, 16.2 mmol) was added to a stirred solution of oxalyl chloride (1 mL, 10.8 mmol) in dichloromethane (60 mL) at −78° C. After 10 minutes, a dichlotomethane solution of 6-(benzyloxymethyl)tetrahydro-2H-pyran-3-ol (14) (1.20 g, 5.40 mmol) was added. Stirring was continued for one hour then triethylamine (3.8 mL, 27 mmol) was added and slowly warmed to 0° C. The reaction was poured into saturated NH4Cl solution and the organic phase was washed with brine and dried (NaSO4). The residue was purified over silica gel using EtOAc and hexanes to give 6-(benzyloxymethyl)dihydro-2H-pyran-3(4H)-one (15).

Aufarbeitung

  1. waitwas continued for one hour
  2. washthe organic phase was washed with brine
  3. dry with materialdried (NaSO4)
  4. customThe residue was purified over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-c1f36ece35b8490a87ba36277688477d
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569283B2

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