4-Iodotoluene → Ethyl 2-(4-(p-tolylethynyl)phenoxy)acetate

HRID 2042969Notes

Reaction equation

HRID 2042969 reaction equation
[C:1]([C:3]1[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][CH:4]=1)#[CH:2].I[C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1>>[C:20]1([CH3:23])[CH:21]=[CH:22][C:17]([C:2]#[C:1][C:3]2[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][CH:4]=2)=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 122074-IodotolueneHCID 22450859Ethyl 2-(4-ethynylphenoxy)acetate

Product 1

HCID 25150214Ethyl 2-(4-(p-tolylethynyl)phenoxy)acetate

Procedure

The title compound was prepared from ethyl (4-ethynylphenoxy)acetate (41 mg, 0.20 mmol) and iodo-4-methylbenzene (46 mg, 0.21 mmol) according to the general procedure ID to give 47 mg (79%) of an orange oil after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:10). Rf: 0.14 (EtOAc:hexanes, 1:10); 1HNMR (CDCl3) δ 7.49-7.37 (m, 4H), 7.17-7.11 (m, 2H), 6.91-6.84 (m, 2H), 4.63 (s, 2H), 4.29-4.26 (dq, 2H, J=7.2 Hz, 2.1 Hz), 2.36 (s, 3H), 1.32-1.27 (tt, 3H, J=7.2 Hz, 1.5 Hz); 13CNMR (CDCl3) δ 168.6, 157.6, 138.1, 133.0, 131.4, 129.1, 120.3, 116.8, 114.7, 88.6, 88.3, 65.4, 61.5, 21.5, 14.1; EI-MS m/z 294 (M+).

Sources & evidence

ORD record
ord-a4b2384d5cd7406e8d14b422405c71ae
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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