1-Undecyn-3-ol → 6-[1-[6-(3-Hydroxy-undec-1ynyl)-pyridine-2yl]-methyl-]pyran-2-one

HRID 1197183Notes

Reaction equation

[OH:1][CH:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:3]#[CH:4].Br[C:14]1[N:19]=[C:18]([CH2:20][C:21]2[O:26][C:25](=[O:27])[CH:24]=[CH:23][CH:22]=2)[CH:17]=[CH:16][CH:15]=1>C(N(CC)CC)C>[OH:1][CH:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:3]#[C:4][C:14]1[N:19]=[C:18]([CH2:20][C:21]2[O:26][C:25](=[O:27])[CH:24]=[CH:23][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 55 °C

Procedure

3-Hydroxy-undec-1-yne (202 mg, 1.2 mmole) and 6-[1-[6-bromopyridine-2yl]methyl]pyran-2-one (270 mg, 1 mmole) are combined in 4 ml triethylamine in a 25 ml one-neck round bottom flask under argon. The mixture is treated with (bis)triphenylphosphine palladium dichloride (14 mg, 0.02 mmole), warmed to 55° C., and is treated with cuprous iodide (2 mg, 0.01 mmole). The reaction mixture is stirred one hour at 55° C., cooled to room temperature, and the volatiles are removed in vacuo. The residue is partitioned between 1×10 ml diethyl ether and 1×10 ml saturated sodium chloride/ammonium chloride (1:1). The aqueous layer is extracted with 3×10 ml diethyl ether. The combined organics are dried over magnesium sulfate and concentrated in vacuo to a brown oil.

Workup

temperaturecooled to room temperature
customthe volatiles are removed in vacuo
customThe residue is partitioned between 1×10 ml diethyl ether and 1×10 ml saturated sodium chloride/ammonium chloride (1:1)
extractionThe aqueous layer is extracted with 3×10 ml diethyl ether
dry with materialThe combined organics are dried over magnesium sulfate
concentrationconcentrated in vacuo to a brown oil

Sources & evidence

ORD record: ord-4d8a5a9607aa4ee49ec6547916070ec4
Source dataset: uspto-grants-1992_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05116981

Reaction notes

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