N-Hydroxyphthalimide → Benzyl 5-[3-(1,3-dioxoisoindolin-2-yloxy)propoxy]-3-chlorobenzoate

HRID 1698860Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1698860
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([O:18][CH2:19][CH2:20][CH2:21][OH:22])[CH:17]=1)[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[N:43]1[C:47](=[O:48])[C:46]2=[CH:49][CH:50]=[CH:51][CH:52]=[C:45]2[C:44]1=[O:53].N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[O:53]=[C:44]1[C:45]2[C:46](=[CH:49][CH:50]=[CH:51][CH:52]=2)[C:47](=[O:48])[N:43]1[O:22][CH2:21][CH2:20][CH2:19][O:18][C:16]1[CH:17]=[C:2]([Cl:1])[CH:3]=[C:4]([CH:15]=1)[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]

Komponenten

6

Edukt 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18322176Benzyl 3-chloro-5-(3-hydroxypropoxy)benzoate

Produkt 1

HCID 18322169Benzyl 5-[3-(1,3-dioxoisoindolin-2-yloxy)propoxy]-3-chlorobenzoateAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of alcohol 26 (5.96 g, 18.6 mmol), triphenylphosphine (5.40 g, 20.5 mmol), and N-hydroxyphthalirnide (2.10 g, 20.5 mmol) in tetrahydrofuran (186 mL) was cooled to 0° C. and reacted slowly with diethyl azodicarboxylate (3.50 mL, 22.3 mmol). After warming to ambient temperature and stirring 16 hrs, the reaction was concentrated in vacuo and purified by chromatography on silica gel (10% ethyl acetate in hexanes) giving product 27 (5.18 g, 60%). 1H NMR (300 MHz, CDCl3) δ 7.83 (dd, 2H, J=5.6 Hz, 3.1 Hz), 7.75 (dd, 2H, J=5.6 Hz, 3.1 Hz), 7.63 (t, 1H, J=1.5 Hz), 7.51 (dd, 1H, J=2.4 Hz, 1.4 Hz), 7.40 (m, 5H), 7.12 (t, 1H, J=2.3 Hz), 5.35 (s, 2H), 4.41 (t, 2H, J=6.1 Hz), 4.28 (t, 2H, J=6.1 Hz), 2.25 (pentet, 2H, J=6.1 Hz).

Aufarbeitung

  1. concentrationthe reaction was concentrated in vacuo
  2. custompurified by chromatography on silica gel (10% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-8250fae45fd7470892bbf7e209111e20
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06344466B2

Notizen zur Reaktion

Wird geladen…