Triethylamine → Toluene-4-sulfonic acid 4-phenyl-but-3-ynyl ester

HRID 1280751Notes

Reaction equation

HRID 1280751 reaction equation
[CH2:1]([OH:5])[CH2:2][C:3]#[CH:4].[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([O-:16])(=[O:15])=O)=[CH:9][CH:8]=1.I[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1.C(OC(=O)C)C.[Cu]I.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>[C:18]1([C:4]#[C:3][CH2:2][CH2:1][O:5][S:13]([C:10]2[CH:9]=[CH:8][C:7]([CH3:6])=[CH:12][CH:11]=2)(=[O:15])=[O:16])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 11575IodobenzeneHCID 1317234903-Butyn-1-ol 4-methylbenzenesulfonate

Product 1

HCID 13125083Toluene-4-sulfonic acid 4-phenyl-but-3-ynyl esterYield 58.3%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture containing 3-butyn-1-ol 4-methylbenzenesulfonate (0.45 g, 2 mmol), iodobenzene (0.45 g, 2.2 mmol), CuI (0.038 g, 0.2 mmol), triethylamine (1.01 g, 10 mmol) and tetrakis(triphenylphosphine)palladium (0.12 g, 0.1 mmol) in toluene (10 ml) was stirred 30 minutes at room temperature, and 2 hours at 65° C. The reaction mixture was cooled to room temperature, diluted with ethylacetate (10 ml), washed with H2O (10 ml), dried over Na2SO4, and concentrated. The residue was chromatographed over silica gel (hexane-ethylacetate 9:1 then 4:1) to provide toluene-4-sulfonic acid 4-phenyl-but-3-ynyl ester (0.35 g, 58%) as a brown oil, MS: m/e=300 (M+).

Workup

  1. custom2 hours
  2. customat 65° C
  3. temperatureThe reaction mixture was cooled to room temperature
  4. washwashed with H2O (10 ml)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was chromatographed over silica gel (hexane-ethylacetate 9:1

Sources & evidence

ORD record
ord-64241294d4084f708dcb8cced775b9bb
Source dataset
uspto-grants-2002_09
Patent number
US06451819B2

Reaction notes

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