Propargyl alcohol → HCID 67486242, compound

HRID 644560Notes

Reaction equation

I[C:2]1[C:7]2[N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:9]=[N:10][C:6]=2[CH:5]=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=1.[CH2:21]([OH:24])[C:22]#[CH:23].[Cl-].[NH4+]>N1CCCC1.[Cu]I>[OH:24][CH2:21][C:22]#[C:23][C:2]1[C:7]2[N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:9]=[N:10][C:6]=2[CH:5]=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a stirred solution of 7-iodo-1-phenyl-5-trifluoromethylbenzimidazole (9.7 g, 25 mmol) and tetrakis (triphenylphosphine)palladium(0) (2.9 g, 5 mmol) in pyrrolidine (75 ml) was added a solution of 2-propyn-1-ol (5.6 g, 0.1 mol) in pyrrolidine (75 ml), then copper (I) iodide (475 mg, 2.5 mmol). The resulting solution was heated to 75° C. with stirring under nitrogen. After 5 h the reaction mixture was allowed to cool, treated with saturated aqueous ammonium chloride and extracted with diethyl ether. The combined organic extracts were dried over anhydrous sodium sulphate and the solvent removed under reduced pressure to leave a residue (14.5 g). This residue was flash chromatographed over silica gel (eluted with dichloromethane/diethyl ether 4:1) to give the desired product (2.53 g, 32%) m/z, 316.8 (M+H)+.

Workup

temperatureto cool
extractionextracted with diethyl ether
dry with materialThe combined organic extracts were dried over anhydrous sodium sulphate
customthe solvent removed under reduced pressure

Sources & evidence

ORD record: ord-3bd7213e7eb54c63bd5187fc597e87a0
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700638B2

Reaction notes

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