Dibenzyl ether → 6-Benzyloxyhexanal

HRID 530276Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 530276
[CH2:1]([O:8][CH2:9][C:10]1C=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.IC1C=CC=C(CC([O-])=[O:25])C=1CC([O-])=O>C(Cl)Cl>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 7657Dibenzyl etherHCID 219456882-[2-(Carboxylatomethyl)-3-iodophenyl]acetate

Produkt 1

HCID 3898776-Benzyloxyhexanal

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. customOn completion of the reaction (
  2. customwas quenched with dilute solution of Na2S2O3
  3. extractionThe organic layer was extracted in DCM
  4. washwashed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe solvent was removed in vacuum
  7. concentrationconcentrated
  8. customsubjected for chromatographic separation

Quellen und Nachweise

ORD-Eintrag
ord-47158f6f297144b6982820657352f70b
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353077B2

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