m-Chloroperbenzoic acid → (E)-N-ethyl-N-(6,6-dimethyl-2-hepten-4-ynyl)-2-hydroxy-5-[3-(3-thienyl)phenoxy]pentylamine
Reaction equation
[O:1]1[CH:3]([CH2:4][CH2:5][CH2:6][O:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[CH:18]=[CH:17][S:16][CH:15]=3)[CH:9]=2)[CH2:2]1.C(OC1C=C(C2C=CSC=2)C=CC=1)CCC=C.S1C=CC(C2C=C(O)C=CC=2)=C1.BrCCCC=C.ClC1C=CC=C(C(OO)=O)C=1.Cl.[CH2:66]([NH:68][CH2:69]/[CH:70]=[CH:71]/[C:72]#[C:73][C:74]([CH3:77])([CH3:76])[CH3:75])[CH3:67]>C1C=CC=CC=1.C(O)C.C(N(CC)CC)C>[CH2:66]([N:68]([CH2:2][CH:3]([OH:1])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:18]=[CH:17][S:16][CH:15]=2)[CH:9]=1)[CH2:69]/[CH:70]=[CH:71]/[C:72]#[C:73][C:74]([CH3:75])([CH3:77])[CH3:76])[CH3:67]Participants
10
Reactant 6
Product 1
Reagents, catalysts & solvents 3
Procedure
0.22 g of 1,2-epoxy-5-[3-(3-thienyl)phenoxy]pentane [synthesized by the epoxidation reaction of 3-[3-(4-pentenyloxy)phenyl]thiophene, prepared from 3-(3-thienyl)phenol and 5-bromo-1-pentene, with m-chloroperbenzoic acid in benzene] was dissolved in 4 ml of ethanol, and 0.22 g of (E)-N-ethyl-6,6-dimethyl-2-hepten-4-ynylamine hydrochloride, 0.34 ml of triethylamine were added. The mixture was refluxed for 5 hours, and then the solvent was evaporated. The residue was purified by silica gel column chromatography [chloroform / ethyl acetate=20/1] to give 0.23 g of the captioned compound as a pale yellow oil.
Workup
- temperatureThe mixture was refluxed for 5 hours
- customthe solvent was evaporated
- customThe residue was purified by silica gel column chromatography [chloroform / ethyl acetate=20/1]
Sources & evidence
- ORD record
- ord-6877d3bd11574149bb032746a6663774
- Source dataset
- uspto-grants-1994_04
- Patent number
- US05306728
Reaction notes
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