Ethyl Acetate → {4-[5-Tert-butyl-4-isopropoxy-2-methyl-3-(3-trimethylsilanyl-prop-2-ynyl)-phenylethynyl]-phenyl}-acetic acid methyl ester

HRID 1869999Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:30])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:16]([O:23][CH:24]([CH3:26])[CH3:25])=[C:15]([CH2:27]Br)[C:14]=2[CH3:29])=[CH:7][CH:6]=1.[CH3:31][Si:32]([C:35]#[CH:36])([CH3:34])[CH3:33].C(OCC)(=O)C>C(N(CC)CC)C.CN(C)C=O.CCCCCC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:30])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:16]([O:23][CH:24]([CH3:26])[CH3:25])=[C:15]([CH2:27][C:36]#[C:35][Si:32]([CH3:34])([CH3:33])[CH3:31])[C:14]=2[CH3:29])=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A solution of [4-(3-bromomethyl-5-tert-butyl-4-isopropoxy-2-methyl-phenylethynyl)-phenyl]-acetic acid methyl ester (Intermediate 148, 0.12 g, 0.25 mmol) in triethyl amine (1 mL) and N,N-dimethylformamide (4 mL) was sparged with argon and treated with trimethylsilylacetylene (0.5 mL, 3.5 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.025 g, 0.036 mmol). The resulting reaction mixture was heated at 85° C. overnight at the end of which it was cooled to ambient temperature and subjected to flash column chromatography over silica gel (230-400 mesh) using 4% ethyl acetate in hexane as the eluent followed by preparative normal phase HPLC using 3% ethyl acetate in hexane as the mobile phase to afford the title compound as an oil (0.038 g, 31%).

Workup

customThe resulting reaction mixture
temperaturewas cooled to ambient temperature

Sources & evidence

ORD record: ord-6abf8d9f90fa41f78b707863ed9bea73
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07638648B2

Reaction notes

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