1-Undecyn-3-ol → 3-[6-(3-Hydroxy-1-undecynyl)-2-pyridinyl]-oxiranebutanol
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].[O:13]1[CH:20]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23](Br)[N:22]=2)[CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][OH:19]>>[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:23]1[N:22]=[C:21]([CH:20]2[O:13][CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][OH:19])[CH:26]=[CH:25][CH:24]=1Participants
Conditions
- Temperature
- 55 °C
Procedure
3-Hydroxy-undec-1-yne (33 mg, 0.194 mmole) and 5,6-epoxy-6[6-bromopyridine-2yl]hexane-1-ol (44 mg, 0.162 mmole) are combined in 1 ml degassed triethylamine in a 25 ml one-neck round bottom flask under argon. The solution is treated with (bis)triphenylphosphine palladium dichloride (3 mg, 0.004 mmole), warmed to 55° C., and is treated with cuprous iodide (1 mg, 0.005 mmole). The reaction mixture is stirred 1.5 hours 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 further extracted with 3×10 ml diethyl ether. The combined organics are dried over magnesium sulfate and concentrated in vacuo to a pale oil.
Workup
- customdegassed triethylamine in a 25 ml one-neck round bottom flask under argon
- 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 further extracted with 3×10 ml diethyl ether
- dry with materialThe combined organics are dried over magnesium sulfate
- concentrationconcentrated in vacuo to a pale oil
Sources & evidence
- ORD record
- ord-133cb9120f7c4c9c9e645cf53456bc34
- Source dataset
- uspto-grants-1992_05
- Patent number
- US05116981
Reaction notes
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