Phenylacetylene → HCID 58319092, compound

HRID 2042972Notes

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]1([C:20]#[CH:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[C:14]1([C:20]#[C:21][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:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Reactant 2

HCID 10821Phenylacetylene

HCID 554150Methyl 3-(4-iodophenyl)propanoate

Product 1

HCID 58319092HCID 58319092, compound

Procedure

The title compound was prepared from methyl 3-(4-iodophenyl)propanoate (100 mg, 0.34 mmol) and phenylacetylene (0.04 mL, 0.36 mmol) according to the general procedure IA to give 66 mg (72%) of a brown oil after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:10). Rf: 0.31 (EtOAc:hexanes, 1:5); 1HNMR (CDCl3) δ 7.53-7.50 (m, 2H), 7.47-7.44 (m, 2H), 7.34-7.32 (m, 3H), 7.19-7.16 (m, 2H), 3.66 (s, 3H), 2.98-2.93 (t, 2H, J=7.5 Hz), 2.66-2.61 (t, 2H, J=7.5 Hz); 13CNMR (CDCl3) δ 173.1, 140.8, 131.7, 131.5, 128.3, 128.3, 128.1, 123.3, 121.2, 89.3, 89.1, 51.6, 35.4, 30.8; ESI-MS m/z 287.1 (MNa+).

Sources & evidence

ORD record: ord-7c8bdda3cb0743e59999a3a85739514f
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586607B2

Reaction notes

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