Triethylamine → 4,4,5,5-tetramethyl-2-{(E)-2-[4-(1-methylethyl)phenyl]ethenyl}-1,3,2-dioxaborolane

HRID 1747896Notes

Reaction equation

C(N(CC)CC)C.[C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]([CH3:18])[CH3:17])=[CH:12][CH:11]=1)#[CH:9].[CH3:19][C:20]1([CH3:27])[C:24]([CH3:26])([CH3:25])[O:23][BH:22][O:21]1>[H-].[Cl-].[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Zr+2].CCCCCC>[CH3:19][C:20]1([CH3:27])[C:24]([CH3:26])([CH3:25])[O:23][B:22](/[CH:9]=[CH:8]/[C:10]2[CH:15]=[CH:14][C:13]([CH:16]([CH3:18])[CH3:17])=[CH:12][CH:11]=2)[O:21]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of triethylamine (246 mg), 1-ethynyl-4-isopropylbenzene (3500 mg), 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3417 mg) and zirconocene chloride hydride (626 mg) was stirred at 80° C. overnight. To the reaction mixture was added hexane, and the mixture was filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (6030 mg) as a yellow solid.

Workup

filtrationthe mixture was filtered
concentrationThe filtrate was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-346c206c78814d9c9ea001db58c115af
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150591B2

Reaction notes

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