2-Iodotoluene → HCID 58319119, compound

HRID 2043007Notes

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]=[CH:19][C:18]=1[CH3:23]>>[C:18]1([CH3:23])[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:2]#[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

Participants

Reactant 2

HCID 51282-Iodotoluene

HCID 58319131Methyl 2-(4-ethynylphenyl)cyclopropanecarboxylate

Product 1

HCID 58319119HCID 58319119, compound

Procedure

The title compound was prepared from methyl 2-(4-ethynylphenyl)cyclopropanecarboxylate (80 mg, 0.40 mmol) and 1-iodo-2-methylbenzene (113 mg, 0.56 mmol) according to the general procedure IF to give 45 mg (39%) of a pale yellow solid after purification by flash chromatography (SiO2, EtOAc:PE, 1:10): Rf=0.41 (EtOAc:PE, 1:4); 1H NMR (CDCl3) δ 7.52-7.41 (m, 3H), 7.25-7.20 (m, 2H), 7.20-7.12 (m, 1H), 7.07 (d, J=8.2 Hz, 2H), 3.72 (s, 3H), 2.57-2.51 (m, 1H), 2.50 (s, 3H), 1.92 (ddd, J=8.5, 5.3, 4.2 Hz, 1H), 1.63 (dt, J=9.2, 5.0 Hz, 1H), 1.33 (ddd, J=8.4, 6.5, 4.7 Hz, 1H); 13C NMR (CDCl3) δ 173.6, 140.3, 140.2, 131.8, 131.6, 129.5, 128.3, 126.2, 125.6, 123.0, 121.7, 93.1, 88.5, 52.0, 26.2, 24.2, 20.8, 17.2; ESI-MS m/z 313.1 (M+Na+).

Sources & evidence

ORD record: ord-4aab112d90da4324aa299c829894fa70
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586607B2

Reaction notes

Loading…