Water → HCID 178451016, Verbindung

HRID 1420883

Reaktionsgleichung

Reaktionsgleichung von HRID 1420883
[OH:1][PH:2]([CH2:4][CH:5]([CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[O:3].[C:22](O)([CH3:25])([CH3:24])[CH3:23].C(N=C=NCCCN(C)C)C.O>ClCCl.CN(C)C1C=CN=CC=1>[C:22]([O:3][PH:2]([CH2:4][CH:5]([CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:6]([O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:7])=[O:1])([CH3:25])([CH3:24])[CH3:23]

Komponenten

7

Edukt 4

HCID 962WaterHCID 6386tert-ButanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 178451017HCID 178451017, Verbindung

Produkt 1

HCID 178451016HCID 178451016, VerbindungAusbeute 70,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of di-tert-butyl 2-[(hydroxyphosphinyl)methyl]pentane-1,5-dioate (315 g, 0.977 mol) in dichloromethane (1000 ml) cooled in an ice bath and under nitrogen were added tert-butanol (123.1 g, 1.66 mol), 4-dimethylaminopyridine (1 g, 8.2 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (281 g, 1.47 mol) . The reaction was allowed to stir overnight. Water was added to the reaction mixture and the dichloromethane layer was retained and dried, and the solvent was removed under reduced pressure. The resulting residue was purified by column chromatography and the desired product was eluted with 1:1 to 2:3 hexane/ethyl acetate. The fractions containing product were concentrated under reduced pressure leaving a clear oil (260 g, 70%). 1H NMR (CDCl3): δ 1.4 (m, 27H) , 1.8 (m, 1H), 1.9 (m, 2H) 2.1 (m, 1H), 2.3 (m, 2H), 2.7-2.8 (m, 1H), 6.7 & 8.0 (d, 1H, the P-H).

Aufarbeitung

  1. customdried
  2. customthe solvent was removed under reduced pressure
  3. customThe resulting residue was purified by column chromatography
  4. washthe desired product was eluted with 1:1 to 2:3 hexane/ethyl acetate
  5. additionThe fractions containing product
  6. concentrationwere concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9643e010a9c34c67b18b3d0e495c04ce
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06071965

Verknüpfte Notizen

Wird geladen…