Trimethylsilylacetylene → HCID 19379151, compound

HRID 2210585Notes

Reaction equation

HRID 2210585 reaction equation
I[C:2]1[C:11]([NH:12][C:13](=[O:15])[CH3:14])=[C:10]([Cl:16])[CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[C:3]=1[OH:17].[CH3:18][Si:19]([C:22]#[CH:23])([CH3:21])[CH3:20]>CCN(CC)CC.O1CCOCC1.[Cu]I>[CH3:18][Si:19]([C:22]#[C:23][C:2]1[C:11]([NH:12][C:13](=[O:15])[CH3:14])=[C:10]([Cl:16])[CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[C:3]=1[OH:17])([CH3:21])[CH3:20]

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 11036030Methyl 4-acetamido-5-chloro-2-hydroxy-3-iodobenzoate

Product 1

HCID 19379151HCID 19379151, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of methyl 3-iodo-4-acetamido-5-chlorosalicylate (2 g) in distilled Et3N (60 ml) and dioxane (40 ml), trimethylsilylacetylene (1 ml), CuI (23 mg), and PdCl2 (PPh3)2 (152 mg) were added. The reaction mixture was stirred at 40° C. for 1.5 hours, after which time the solvents were removed in vacuo. A sample of the residue was purified by column chromatography for analytical purposes eluting with diethyl ether/hexane mixtures to yield the intermediate methyl 3-trimethylsilylethynyl-4-acetamido-5-chloro-salic ylate.

Workup

  1. customafter which time the solvents were removed in vacuo
  2. customA sample of the residue was purified by column chromatography for analytical purposes
  3. washeluting with diethyl ether/hexane

Sources & evidence

ORD record
ord-80bef94b178c4672ba111c1bdedf94da
Source dataset
uspto-grants-1995_10
Patent number
US05459161

Reaction notes

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