Reaktion #617458

Reaktionsgleichung

alcohol

mono-benzyl ether

iodobenzenediacetate

→

6-(benzyloxy)hexanal

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeOn completion of the reaction (
2. 2
   Sonstigewas quenched with dilute solution of Na2S2O3
3. 3
   ExtraktionThe organic layer was extracted in DCM
4. 4
   Waschenwashed with brine
5. 5
   Trocknendried over anhydrous Na2SO4
6. 6
   SonstigeThe solvent was removed in vacuum
7. 7
   Einengenconcentrated
8. 8
   Sonstigesubjected for chromatographic separation

Vorschrift

To a solution of alcohol (22, 6-(benzyloxy)hexan-1-01) dissolved in dry DCM, Tempo free radical (0.1 equiv), iodobenzenediacetate (1.1 equiv) were added and stirred at 25° C. On completion of the reaction (by checking TLC), it was quenched with dilute solution of Na2S2O3. The organic layer was extracted in DCM, washed with brine, dried over anhydrous Na2SO4. The solvent was removed in vacuum concentrated and subjected for chromatographic separation. The eluent was allowed to come in a solution of pet ether:EtOAC=95:5 as a colorless liquid. 1H NMR (CDCl3, 200 MHz): δ 9.8 (s, 1H), 7.2-7.4 (m, 5H), 4.5 (s, 2H), 3.5 (t, 2H), 2.4 (t, 2H), 1.6 (m, 4H), 1.4 (m, 4H); 13C NMR (CDCl3, 50 MHz): δ 202.75, 138.50, 128.40, 127.68, 127.50, 72.95, 70.03, 43.86, 29.53, 25.85, 21.91.

Quelle