N-Hydroxyphthalimide → Triphenylphosphine Oxide

HRID 2424330Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2424330
CC[O:3]C(/N=N/C(OCC)=O)=O.C(OC(=O)CCCCCCCCCCCO)C1C=CC=CC=1.[C:35]1([P:41]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.ON1C(=O)C2=CC=CC=C2C1=O>C1COCC1.CCCCCC.C(OC(=O)C)C>[C:48]1([P:41](=[O:3])([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1

Komponenten

7

Edukt 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 12077613Dodecanoic acid, 12-hydroxy-, phenylmethyl ester

Produkt 1

HCID 13097Triphenylphosphine Oxide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

Diethylazodicarboxylate (DEAD, 16.96 ml, 107.7 mmol) was added dropwise to the mixture of 12-Hydroxydodecanoic acid benzyl ester (21 g, 71.8 mmol), triphenylphosphine (28.29 g, 107.7 mmol) and N-hydroxyphthalimide (12.88 g, 78.98 mmol) in absolute THF (250 ml) at −20°-−30° C. under stirring. The reaction mixture was stirred at this temperature for additional 2-3 h, after which time TLC (hexane-ethylacetate 3:1) indicated reaction completion. The solvent was removed in vacuo and the residue was treated ether (250 ml). Formed precipitate of triphenylphosphine oxide was filtered off, mother liquor was evaporated to dryness and the residue was dissolved in methylene chloride and purified by flash chromatography on silica gel in hexane-ethyl acetate (7:3). Appropriate fractions were pooled and evaporated to dryness to afford 26.5 g (84.4%) of compound 15.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at this temperature for additional 2-3 h
  2. customreaction completion
  3. customThe solvent was removed in vacuo
  4. additionthe residue was treated ether (250 ml)

Quellen und Nachweise

ORD-Eintrag
ord-5c5c0ff74ef3449fb483451c92ce4e60
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07964578B2

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