1,1,3,3-Tetramethylguanidine → HCID 57925910, Verbindung

HRID 1013463Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1013463
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]Br)=[CH:6][CH:5]=1.[CH3:13][C:14]1([CH3:21])[CH2:19][O:18][PH:17](=[O:20])[O:16][CH2:15]1.CN(C)C(N(C)C)=N>C1(C)C=CC=CC=1.Cl>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][P:17]2(=[O:20])[O:18][CH2:19][C:14]([CH3:21])([CH3:13])[CH2:15][O:16]2)=[CH:6][CH:5]=1

Komponenten

6

Edukt 3

HCID 664601,1,3,3-TetramethylguanidineHCID 777171,3,2-Dioxaphosphorinane, 5,5-dimethyl-, 2-oxideHCID 256687Methyl 4-(bromomethyl)benzoate

Produkt 1

HCID 57925910HCID 57925910, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

4-Bromomethyl-benzoic acid methyl ester (0.50 g, 2.18 mmol) was made 2.0 M in anhydrous toluene and to this mixture was added 5,5-dimethyl-[1,3,2]dioxaphosphinane 2-oxide (0.66 g, 4.37 mmol) followed by N,N,N′,N′-tetramethyl-guanidine (0.25 g, 2.18 mmol). The mixture was stirred at ambient temperature for 18 hours. The reaction mixture was then diluted with 1N aq HCl and extracted with EtOAc. The organic layer was again washed with 1 N aqueous HCl, brine, dried (MgSO4) then concentrated in vacuo. The residue was purified by MPLC (0-70% EtOAc in CH2Cl2) to afford the title compound: MS: cal'd 299 (MH+), exp 299 (MH+)

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe organic layer was again washed with 1 N aqueous HCl, brine
  3. dry with materialdried (MgSO4)
  4. concentrationthen concentrated in vacuo
  5. customThe residue was purified by MPLC (0-70% EtOAc in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-259ed4bfbc024b128f29dcd5b08dc25c
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981874B2

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