tert-Butyl bromoacetate → Tert-butyl 3,3-bis(dimethoxyphosphoryl)propanoate

HRID 578726Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 578726
[CH3:1][O:2][P:3]([CH2:7][P:8]([O:12][CH3:13])([O:10][CH3:11])=[O:9])([O:5][CH3:6])=[O:4].Br[CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].CC(C)([O-])C.[K+]>C1COCC1>[C:19]([O:18][C:16](=[O:17])[CH2:15][CH:7]([P:3]([O:5][CH3:6])([O:2][CH3:1])=[O:4])[P:8]([O:10][CH3:11])([O:12][CH3:13])=[O:9])([CH3:22])([CH3:21])[CH3:20]

Komponenten

5

Edukt 3

HCID 79177tert-Butyl bromoacetateHCID 519206Tetramethyl methylenediphosphonateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 89454165Tert-butyl 3,3-bis(dimethoxyphosphoryl)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To an ice cooled solution of bis(dimethoxyphosphoryl)methane (4.64 g, 20 mmol) and tert-butyl bromoacetate (7.35 ml, 50 mmol) in dry THF (40 ml) under nitrogen was added potassium tert-butoxide (5.8 g, 43 mmol). The reaction mixture was stirred at room temperature overnight and then quenched with 4 ml of saturated ammonium chloride. The volatiles were removed in vacuum and by two cycles of toluene addition and evaporation. Flash chromatography in dichloromethane:methanol, 95:5 on gave the product as an oil. Yield 4.0 g.

Aufarbeitung

  1. customquenched with 4 ml of saturated ammonium chloride
  2. customThe volatiles were removed in vacuum and by two cycles of toluene addition and evaporation

Quellen und Nachweise

ORD-Eintrag
ord-030086b6f85441838121b3c9ce6dd57d
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040637B2

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