m-Ethynylphenol → Methyl 3-(4-((3-hydroxyphenyl)ethynyl)phenyl)propanoate

HRID 2043018Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[C:14]([C:16]1[CH:17]=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=1)#[CH:15]>>[OH:22][C:18]1[CH:17]=[C:16]([C:14]#[C:15][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=2)[CH:21]=[CH:20][CH:19]=1

Participants

Reactant 2

HCID 139144m-Ethynylphenol

HCID 554150Methyl 3-(4-iodophenyl)propanoate

Product 1

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

Procedure

The title compound was prepared from methyl 3-(4-iodophenyl)propanoate (100 mg, 0.34 mmol) and 3-ethynylphenol (0.025 mL, 0.38 mmol) according to the general procedure IC to give 66 mg (69%) of a light brown solid after purification by flash chromatography (SiO2, EtOAc:PE, 1:6→1:0). Rf=0.24 (EtOAc:PE; 1:2); 1H NMR (CDCl3): δ 7.43 (d, J=8.0 Hz, 2H), 7.20-7.15 (m, 3H), 7.10-7.08 (m, 1H), 7.00-6.99 (m, 1H), 6.84-6.80 (m, 1H), 5.50 (br, 1H), 3.68 (s, 3H), 2.96 (t, J=8.0 Hz, 2H), 2.64 (t, J=8.1 Hz, 2H); 13C NMR (CDCl3): δ 173.7, 155.7, 141.0, 132.0, 129.8, 128.5, 124.7, 124.4, 121.3, 118.4, 115.9, 89.4, 89.0, 52.0, 35.6, 31.0; ESI-MS m/z 303.0 (M+Na+).

Sources & evidence

ORD record: ord-3b32931a38884d3c9d55a63ea0d4c9f4
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586607B2

Reaction notes

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