4-((Trimethylsilyl)ethynyl)phenol → 1,4-Bis(4-hyroxyphenyl)-1,2,3-triazole

HRID 340854

Reaktionsgleichung

C[Si](C)(C)[C:3]#[C:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[N:14]([C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)=[N+:15]=[N-:16].N(C1C=C(O)C=CC=1)=[N+]=[N-]>>[OH:23][C:20]1[CH:21]=[CH:22][C:17]([N:14]2[CH:3]=[C:4]([C:5]3[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=3)[N:16]=[N:15]2)=[CH:18][CH:19]=1

Komponenten

Edukt 3

HCID 107502104-((Trimethylsilyl)ethynyl)phenol

HCID 113670133-Azidophenol

HCID 116223404-Azidophenol

Produkt 1

HCID 710875351,4-Bis(4-hyroxyphenyl)-1,2,3-triazoleAusbeute 60 %

Versuchsvorschrift

4-BPT was prepared in a similar manner as 3-BPT, using 4-TMSE-phenol (3.50 g, 18.4 mmol) and 4-azidophenol (3.73 g, 27.9 mmol) instead of 3-TMSE-phenol and 3-azidophenol. This gave 2.79 g (60% yield) of a purple crystal. 1H NMR (MeOD-d4, 300 MHz, ppm): 8.62 (s, 1H, triazol-H), 7.75-7.68 (m, 4H, Ar—H), 6.99 (d, 2H, J=9.0 Hz, Ar—H), 6.90 (d, 2H, J=8.7 Hz, Ar—H). 13C NMR (MeOD-d4, 75 MHz, ppm): 159.7, 159.3, 149.8, 131.0, 128.4, 123.4, 123.0, 119.4, 117.3, 116.9.

Aufarbeitung

custom4-BPT was prepared in a similar manner as 3-BPT,

Quellen und Nachweise

ORD-Eintrag: ord-c672364d0c9e45c78428fef363f951dd
Quelldatensatz: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08895688B2

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