Reaktion #158446

ord-65086ca25cd44c60bc1357055a651c4f

Reaktionsgleichung

O=CCC1(c2ccccc2)CCCCO1
2-(2-phenyltetrahydro-2H-pyran-2-yl)acetaldehyde
NS(=O)(=O)O
sulfamic acid
[Na+].[O-][Cl+][O-]
sodium chlorite
O=C(O)CC1(c2ccccc2)CCCCO1
2-(2-phenyltetrahydro-2H-pyran-2-yl)acetic acid

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    ExtraktionThen the product was extracted with EtOAc (3×)
  2. 2
    Waschenthe combined extracts were washed with brine
  3. 3
    Trocknendried over Na2SO4
  4. 4
    Sonstigeevaporated

Vorschrift

To a solution of 2-(2-phenyltetrahydro-2H-pyran-2-yl)acetaldehyde (100 mg, 0.490 mmol) and sulfamic acid (57.0 mg, 0.587 mmol) in THF (1.5 mL) was added a solution of sodium chlorite (53.1 mg, 0.587 mmol) in water (1.5 mL) dropwise, and the mixture was stirred at room temperature for 3 hrs. Then the product was extracted with EtOAc (3×) and the combined extracts were washed with brine, dried over Na2SO4, and evaporated to give 2-(2-phenyltetrahydro-2H-pyran-2-yl)acetic acid as oil. LC/MS: m/e 221.14 (M+H)+.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08822510B2uspto-grants-2014_09