Methyl iodide → Methyl 3-(4-((3-methoxyphenyl)ethynyl)phenyl)propanoate

HRID 2043020Notes

Reaction equation

HRID 2043020 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.I[CH3:23]>>[CH3:23][O:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:14][CH:15]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 58319096Methyl 3-(4-((3-hydroxyphenyl)ethynyl)phenyl)propanoate

Product 1

HCID 58319109Methyl 3-(4-((3-methoxyphenyl)ethynyl)phenyl)propanoate

Procedure

The title compound was prepared from methyl 3-(4-((3-hydroxyphenyl)ethynyl)phenyl)propanoate (41 mg, 0.20 mol) and iodomethane (60 μL, 0.97 mmol) according to the general procedure IV to give 38 mg (69%) of a pure yellow oil. Rf=0.37 (EtOAc:PE, 1:3); 1H NMR (CDCl3): δ 7.45 (dt, J=8.3 Hz, 2.0 Hz, 2H), 7.27-7.23 (m, 1H), 7.18 (d, J=8.3 Hz, 2H), 7.12 (dt, J=7.5 Hz, 1.3 Hz, 1H), 7.05 (dd, J=2.8 Hz, 1.5 Hz, 1H), 6.88 (ddd, J=8.4 Hz, 2.4 Hz, 1.0 Hz, 1H), 3.82 (s, 3H), 3.76 (s, 3H), 2.63 (t, J=7.8 Hz, 2H); 13C NMR (CDCl3): δ 173.1, 159.3, 140.9, 131.8, 129.4, 128.3, 124.3, 124.1, 121.1, 116.3, 114.8, 89.1, 89.0, 55.3, 51.6, 35.4, 30.8.

Sources & evidence

ORD record
ord-d1a483333a584c08923f203d0165b3a3
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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