Triethylamine → 2-[6-(tert-Butyl-dimethyl-silanyloxy)-hex-1-enyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

HRID 749638Notes

Reaction equation

[C:1]([Si:5]([O:8][CH2:9][CH2:10][C:11]#[CH:12])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[CH3:13][C:14]1([CH3:21])[C:18]([CH3:20])([CH3:19])[O:17][BH:16][O:15]1.[CH2:22](N(CC)CC)[CH3:23]>[H-].[Cl-].C1([Zr+2]C2C=CC=C2)C=CC=C1>[C:1]([Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:22]=[CH:23][B:16]1[O:17][C:18]([CH3:20])([CH3:19])[C:14]([CH3:21])([CH3:13])[O:15]1)([CH3:3])([CH3:4])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of tert-butyl-but-3-ynyloxy-dimethyl-silane (I) (1.0 g, 7.14 mmol) and 4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (II) (958 mg, 7.49 mmol) were added bis(cyclopentadienyl)zirconium chloride hydride (183 mg, 0.714 mmol) and triethylamine (72 mg, 0.714 mmol). The resulting mixture was heated at 60° C. for 6 hours and was diluted with hexanes. The precipitate was removed by filtering over a short pad of silica gel and washed with hexanes. The filtrate was concentrated and dried through vacuum to give 1.76 g (93%) of the title compound as a colorless liquid.

Workup

customThe precipitate was removed
filtrationby filtering over a short pad of silica gel
washwashed with hexanes
concentrationThe filtrate was concentrated
customdried through vacuum

Sources & evidence

ORD record: ord-6ed94f1ada1a434abaf4285c2a59b800
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07402703B2

Reaction notes

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