Hydrochloric Acid → Phenyl(1-hexynyl)isopropoxyborane

HRID 2291366Notes

Reaction equation

HRID 2291366 reaction equation
[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

Participants

9

Reactant 7

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

Product 1

HCID 13721780Phenyl(1-hexynyl)isopropoxyborane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

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.

Workup

  1. customYield

Sources & evidence

ORD record
ord-0303d7f3447b44bca1daeb533ac66a80
Source dataset
uspto-grants-1989_01
Patent number
US04795821

Reaction notes

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