Diisopropylamine → Methyl 3-hydroxy-4-[2-(trimethylsilyl)ethynyl]benzoate

HRID 408566Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1I)[C:5]([O:7][CH3:8])=[O:6].[CH3:13][Si:14]([C:17]#[CH:18])([CH3:16])[CH3:15].C(NC(C)C)(C)C>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu](I)I>[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:18]#[C:17][Si:14]([CH3:16])([CH3:15])[CH3:13])[C:5]([O:7][CH3:8])=[O:6]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl 3-hydroxy-4-iodobenzoate (1 eq.) in dry THF were added trimethylsilylacetylene (5 eq.), tetrakis(triphenylphosphine)palladium (0.03 eq.), copper iodide (0.02 eq.) and diisopropylamine (2.1 eq.) under argon. The reaction mixture was stirred at 60° C. for 15 h, cooled to 20° C. and the solvents removed under reduced pressure. The crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 9/1) to afford methyl 3-hydroxy-4-[(trimethylsilyl)ethynyl]benzoate.

Workup

temperaturecooled to 20° C.
customthe solvents removed under reduced pressure
customThe crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 9/1)

Sources & evidence

ORD record: ord-b0166ceff4a24481bdf1e03737967184
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759334B2

Reaction notes

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