Methylparaben → Methyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)benzoate

HRID 1599925Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1599925
[OH:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14].CCOC(/N=N/C(OCC)=O)=O.O[C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.CN(C=O)C.CCOCC>[C:8]1(=[O:9])[N:4]([CH2:3][CH2:2][O:1][C:28]2[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=2)[C:5](=[O:14])[C:6]2=[CH:13][CH:12]=[CH:11][CH:10]=[C:7]12

Komponenten

8

Edukt 4

HCID 7456MethylparabenHCID 11776TriphenylphosphineHCID 77499N-(2-Hydroxyethyl)phthalimideHCID 5462977Diethyl azodicarboxylate

Produkt 1

HCID 7679064Methyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of N-(2-hydroxyethyl)phthalimide (Aldrich, 19-1, 6.36 g, 33 mmol) and DEAD (5.7 mL, 36 mmol) in 25 mL THF and 10 mL DMF was added to a solution of methyl 4-hydroxybenzoate (1-2, 5.00 g, 33 mmol) and Ph3P (9.53 g, 36 mmol) in 100 mL THF during 1 h. After an additional hour the reaction was diluted with ether, washed twice with water, then 1N NaOH and brine, dried (MgSO4), filtered and concentrated. Flash chromatography (silica gel, CH2Cl2) provided 19-2 as a white solid.

Aufarbeitung

  1. washwashed twice with water
  2. dry with material1N NaOH and brine, dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-fbe41620737a4f6ea3d1662c133903af
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05741796

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