2-Iodophenol → HCID 58319090, compound

HRID 2043024Notes

Reaction equation

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

Participants

Reactant 2

HCID 107842-Iodophenol

HCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Product 1

HCID 58319090HCID 58319090, compound

Procedure

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (102 mg, 0.53 mmol) and 2-iodophenol (130 mg, 0.58 mmol) according to the general procedure IF to give 19 mg (13%) of a white solid after purification by flash chromatography (SiO2, EtOAc:PE, 1:10). Rf=0.28 (EtOAc:PE, 1:5); 1H NMR (CDCl3): δ 7.79 (dt, J=8.3 Hz, 2.0 Hz, 2H), 7.56 (d, J=1.0 Hz, 1H), 7.50 (d, J=1.0 Hz, 1H), 7.29-7.21 (m, 3H), 6.98 (d, J=1.0 Hz, 1H), 3.68 (s, 3H), 2.99 (t, J=7.8 Hz, 2H), 2.60 (t, J=7.8 Hz, 2H); 13C NMR (CDCl3): δ 173.2, 155.9, 154.8, 141.1, 129.3, 128.7, 128.8, 125.1, 124.1, 122.9, 120.9, 111.1, 100.9, 51.6, 35.5, 30.7; ESI-MS m/z 303.1 (M+Na+).

Sources & evidence

ORD record: ord-8591a671372d450ba4723ab6dc5c5fca
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586607B2

Reaction notes

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