3-Iodotoluene → HCID 58319104, compound

HRID 2042975Notes

Reaction equation

HRID 2042975 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]=[C:18]([CH3:22])[CH:17]=1>>[C:18]1([CH3:22])[CH:19]=[CH:20][CH:21]=[C:16]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=2)[CH:17]=1

Participants

3

Reactant 2

HCID 122683-IodotolueneHCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Product 1

HCID 58319104HCID 58319104, compound

Procedure

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (90 mg, 0.48 mmol) and iodo-3-methylbenzene (0.07 mL, 0.55 mmol) according to the general procedure IB to give 42 mg (36%) of an orange oil after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:30→1:10). Rf: 0.29 (EtOAc:hexanes, 1:5); 1HNMR (CDCl3) δ 7.46-7.43 (m, 2H), 7.35-7.31 (m, 2H), 7.22-7.12 (m, 4H), 3.67 (s, 3H), 2.99-2.93 (t, 2H, J=7.8 Hz), 2.66-2.61 (t, 2H, J=7.8 Hz), 2.35 (s, 3H); 13CNMR (CDCl3) δ 173.1, 140.8, 138.0, 132.1, 131.7, 129.1, 128.6, 128.3, 128.2, 123.1, 121.3, 89.3, 88.9, 51.6, 35.4, 30.8, 21.2; ESI-MS m/z 301.1 (MNa+).

Sources & evidence

ORD record
ord-0ec7f9766eee461aaba788720ed894f9
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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