Hydrochloric Acid → Phenyl(1-hexynyl)isopropoxyborane

HRID 2291366Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2291366
[C:1]([Li])#[C:2][CH2:3][CH2:4][CH2:5][CH3:6].C#CCCCC.C([Li])CCC.[C:19]1([B:25](OC(C)C)[O:26][CH:27]([CH3:29])[CH3:28])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl.[B].C=C(C)C>C(OCC)C>[C:6]1([B:25]([C:19]#[C:20][CH2:21][CH2:22][CH2:23][CH3:24])[O:26][CH:27]([CH3:28])[CH3:29])[CH:5]=[CH:4][CH:3]=[CH:2][CH:1]=1

Komponenten

9

Edukt 7

HCID 313Hydrochloric AcidHCID 8255IsobutyleneHCID 127321-HexyneHCID 569210Bis(1-methylethyl) B-phenylboronateHCID 5462311BoronHCID 178418339ButyllithiumHCID 178506798HCID 178506798, Verbindung

Produkt 1

HCID 13721780Phenyl(1-hexynyl)isopropoxyborane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel3×

Versuchsvorschrift

The title compound was prepared following the method of Example 14, using 1-hexynyllithium (64 mmol) prepared from 1-hexyne and n-butyl lithium in ethyl ether (64 mL) and phenyldiisopropoxyborane (11.96 g, 58 mmol) dissolved in ethyl ether (60 mL) and quenched with hydrogen chloride in ethyl ether (18.7 mL, 64 mmol). Yield. 11.2 g (86%), bp 102°-105° C. (0.4 mm Hg); n20D 1.5008; proton NMR (CDCl3) δ7.90 (m, 2H), 7.31 (m, 3H), 4.87 (septet, J=18 Hz, 1H), 2.33 (triplet, J=18 Hz, 2H), 1.23 (d, J=18 Hz, 6H), 0.90 (triplet, 3H); boron NMR (CDCl3) δ+36.5 ppm(s); mass spectrum (chemical ionization, isobutene) m/e 229 (M+H, 10%); IR (thin film) 2195, 1324 cm-1.

Aufarbeitung

  1. customYield

Quellen und Nachweise

ORD-Eintrag
ord-0303d7f3447b44bca1daeb533ac66a80
Quelldatensatz
uspto-grants-1989_01
Patentnummer
US04795821

Notizen zur Reaktion

Wird geladen…