Pyridine 4-methylbenzene-1-sulfonate → 7-Phenylhept-6-yn-1-ol

HRID 269425

Reaktionsgleichung

Reaktionsgleichung von HRID 269425
C1(C)C=CC(S(O)(=O)=O)=CC=1.N1C=CC=CC=1.[C:18]1([C:24]#[C:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][O:31]C2CCCCO2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CO>[C:18]1([C:24]#[C:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][OH:31])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

4

Edukt 2

HCID 161440Pyridine 4-methylbenzene-1-sulfonateHCID 589246782-(7-phenylhept-6-ynyloxy)tetrahydro-2H-pyrane

Produkt 1

HCID 589246797-Phenylhept-6-yn-1-olAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

Pyridine toluene-4-sulphonate (0.75 g, 3 mmol) was added to a magnetically stirred solution of 2-(7-phenylhept-6-ynyloxy)-tetrahydro-2H-pyrane (7) (13.62 g, 50 mmol) in dry methanol (300 mL). The reaction mixture was stirred at 55° C. and monitored by TLC. When all the base material had been converted, methanol was distilled out on a rotary evaporator and water (200 mL) was added to the residue. The aqueous phase was extracted with petroleum ether (boiling point 40-60° C.)/Et2O 1:1 (5×50 mL). The combined organic phases were washed with water (2×20 mL) and dried (MgSO4). Distillation on a rotary evaporator yielded 9.1 g (97%) of a yellow viscous oil. TLC and NMR indicated a pure product.

Aufarbeitung

  1. distillationmethanol was distilled out on a rotary evaporator and water (200 mL)
  2. additionwas added to the residue
  3. extractionThe aqueous phase was extracted with petroleum ether (boiling point 40-60° C.)/Et2O 1:1 (5×50 mL)
  4. washThe combined organic phases were washed with water (2×20 mL)
  5. dry with materialdried (MgSO4)
  6. distillationDistillation
  7. customon a rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-2facfffb0e2d44a9892ae3ed367c9f35
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446226B2

Verknüpfte Notizen

Wird geladen…