3-Iodotoluene → HCID 58319088, compound

HRID 2043008Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:11][CH:10]2[C:12]([O:14][CH3:15])=[O:13])=[CH:5][CH:4]=1)#[CH:2].I[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=1>>[C:19]1([CH3:23])[CH:20]=[CH:21][CH:22]=[C:17]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][C:6]([CH:9]3[CH2:11][CH:10]3[C:12]([O:14][CH3:15])=[O:13])=[CH:5][CH:4]=2)[CH:18]=1

Participants

Reactant 2

HCID 122683-Iodotoluene

HCID 58319131Methyl 2-(4-ethynylphenyl)cyclopropanecarboxylate

Product 1

HCID 58319088HCID 58319088, compound

Procedure

The title compound was prepared from methyl 2-(4-ethynylphenyl)cyclopropanecarboxylate (80 mg, 0.40 mmol) and 1-iodo-3-methylbenzene (60 μL, 0.47 mmol) according to the general procedure IF to give 42 mg (36%) of a pale yellow solid after purification by flash chromatography (SiO2, EtOAc:PE, 1:9): Rf=0.43 (EtOAc:PE, 1:4); 1H NMR (CDCl3) δ 7.43 (d, J=8.3 Hz, 2H), 7.37-7.30 (m, 2H), 7.23 (t, J=7.6 Hz, 1H), 7.14 (d, J=7.6 Hz, 1H), 7.06 (d, J=8.2 Hz, 2H), 3.72 (s, 3H), 2.61-2.45 (m, 1H), 2.35 (s, 3H), 1.92 (ddd, J=8.5, 5.3, 4.3 Hz, 1H), 1.63 (dt, J=9.9, 5.0 Hz, 1H), 1.33 (ddd, J=8.4, 6.5, 4.7 Hz, 1H); 13C NMR (CDCl3) δ 173.6, 140.3, 138.0, 132.2, 131.7, 129.1, 128.6, 128.2, 126.2, 123.1, 121.5, 89.7, 88.8, 52.0, 26.2, 24.2, 21.2, 17.2; ESI-MS m/z 313.1 (M+Na+).

Sources & evidence

ORD record: ord-2a657201695240a69935f50254c4e63e
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586607B2

Reaction notes

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