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Triphenylphosphine → HCID 23434069, Verbindung

HRID 2121730
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2121730
O[CH2:2][C:3]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[S:5][C:4]=1[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:40]([O:44][C:45]([NH:47][O:48][C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])=[O:46])([CH3:43])([CH3:42])[CH3:41].CCOC(/N=N/C(OCC)=O)=O>C1COCC1.O>[C:40]([O:44][C:45]([N:47]([CH2:2][C:3]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=2)[S:5][C:4]=1[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)[O:48][C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])=[O:46])([CH3:43])([CH3:42])[CH3:41]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 2728863tert-Butyl (((1,1-dimethylethoxy)carbonyl)oxy)carbamateHCID 5462977Diethyl azodicarboxylateHCID 23434113HCID 23434113, Verbindung

Produkt 1

HCID 23434069HCID 23434069, VerbindungAusbeute 35,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-hydroxymethyl-2,5-di(4-pyridyl)-4-methylthiophene (0.282 g), triphenylphosphine(0.446 g), and N,O-di-(tert-butoxycarbonyl)hydroxylamine (0.224 g), in THF (20 mL) was added diethylazodicarboxylate (0.296 g) under nitrogen. After stirring for 23 hours, the reaction mixture was poured into water (50 mL) and the whole was extracted with CH2Cl2 (100 mL). The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate-CH2Cl2-MeOH (1:1:0.04). The resulting product was purified by column chromatography on silica(NH-silica gel, FUJI SILISIA CHEMICAL LTD. DM2035)(ethyl acetate-CH2Cl2-MeOH=1:1:0.04) to give the subtitle compound (0.17 g).

Aufarbeitung

  1. extractionthe whole was extracted with CH2Cl2 (100 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography
  6. washeluting with ethyl acetate-CH2Cl2-MeOH (1:1:0.04)
  7. customThe resulting product was purified by column chromatography on silica(NH-silica gel, FUJI SILISIA CHEMICAL LTD. DM2035)(ethyl acetate-CH2Cl2-MeOH=1:1:0.04)

Quellen und Nachweise

ORD-Eintrag
ord-ac307ef08dda4babb1cf74c247daaedf
Quelldatensatz
uspto-grants-2004_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06696470B2

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