Propargyl bromide → Methyl 3-(4-((3-(prop-2-ynyloxy)phenyl)ethynyl)phenyl)propanoate

HRID 2043022Notes

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.Br[CH2:23][C:24]#[CH:25]>>[CH2:25]([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)[C:24]#[CH:23]

Participants

Reactant 2

HCID 7842Propargyl bromide

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

Product 1

HCID 58319133Methyl 3-(4-((3-(prop-2-ynyloxy)phenyl)ethynyl)phenyl)propanoate

Procedure

The title compound was prepared from methyl 3-(4-((3-hydroxyphenyl)ethynyl)phenyl)propanoate (100 mg, 0.45 mmol) and 3-bromoprop-1-yne (129 mg, 0.93 mmol) according to the general procedure IV to give 105 mg (72%) of a pure light brown oily product. Rf=0.56 (EtOAc:PE, 1:1); 1H NMR (CDCl3): δ 7.46 (dt, J=6.3 Hz, 1.8 Hz, 2H), 7.28-7.25 (m, 1H), 7.19, 7.15 (m, 3H), 7.12 (dd, J=2.5 Hz, 1.3 Hz, 1H), 6.96 (ddd, J=8.3 Hz, 2.8 Hz, 1.0 Hz, 1H), 4.70 (d, J=2.5 Hz, 2H), 3.67 (s, 3H), 2.96 (t, J=7.7 Hz, 2H), 2.64 (t, J=7.8 Hz, 2H), 2.54 (t, J=2.4 Hz, 1H); 13C NMR (CDCl3): δ 173.1, 157.3, 141.0, 131.8, 129.4, 128.3, 125.0, 124.4, 121.0, 117.4, 115.6, 89.3, 88.8, 78.3, 75.7, 55.9, 51.6, 35.4, 30.8; MALDI-MS m/z 341.4 (M+Na+).

Sources & evidence

ORD record: ord-ea01ab4726424cce97e3159b19435cbf
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586607B2

Reaction notes

Loading…