Propargyl alcohol → [3-(3-Hydroxyprop-1-ynyl)phenoxy]acetic acid tert-butyl ester

HRID 1352863Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[O:5][CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[CH2:17]([OH:20])[C:18]#[CH:19].C(OCC)(=O)C>C(N(CC)CC)C.[Cu]I.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>[OH:20][CH2:17][C:18]#[C:19][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[O:5][CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Participants

Conditions

Temperature: 70 °C

Procedure

The compound (1.00 g, 3.00 mmol) of Example 22-1 was dissolved in triethylamine (30 ml) under an atmosphere of nitrogen. Thereto were added propargyl alcohol (0.35 ml, 6.00 mmol), copper(I) iodide (6.00 mg, 30.0 μmol) and dichlorobis(triphenylphosphine)palladium (II) (42.0 mg, 60.0 μmol) and the mixture was stirred for 1 hour at 70° C. The mixture was cooled and thereto was added ethyl acetate. The mixture was washed with 10% aqueous citric acid solution, water, an aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution in the order and dried over sodium sulfate. The solvent was removed and purified with silica gel chromatography (hexane:ethyl acetate, 3:1–2:1) to give the subject compound as a yellow oil(537 mg, 68%).

Workup

temperatureThe mixture was cooled
washThe mixture was washed with 10% aqueous citric acid solution, water
dry with materialan aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution in the order and dried over sodium sulfate
customThe solvent was removed
custompurified with silica gel chromatography (hexane:ethyl acetate, 3:1–2:1)

Sources & evidence

ORD record: ord-a2059c51137b4639919fccc3fccc2abe
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220773B2

Reaction notes

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