Phenylacetylene → HCID 25149803, compound

HRID 2042967

Reaction equation

I[C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.[C:15]1([C:21]#[CH:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[C:15]1([C:21]#[C:22][C:2]2[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Reactant 2

HCID 10821Phenylacetylene

HCID 25149802Ethyl 2-(4-iodophenoxy)acetate

Product 1

HCID 25149803HCID 25149803, compound

Procedure

The title compound was prepared from ethyl 2-(4-iodophenoxy)acetate (550 mg, 1.80 mmol) and phenylacetylene (0.17 mL, 1.80 mmol) according to the general procedure IE to give 390 mg (78%) of an orange solid after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:5). Rf: 0.26 (EtOAc:hexanes, 1:5); 1HNMR (CDCl3) δ 7.53-7.45 (m, 4H), 7.36-7.25 (m, 3H), 6.90-6.87 (m, 2H), 4.63 (s, 2H), 4.32-4.23 (dq, 2H, J=7.2 Hz, 2.1 Hz), 1.35-1.24 (tt, 3H, J=7.2 Hz, 1.5 Hz); 13CNMR (CDCl3) δ 168.6, 157.8, 133.1, 131.5, 128.3, 128.0, 123.4, 116.6, 114.7, 89.0, 88.4, 65.4, 61.5, 14.1; EI-MS m/z 280 (M+).

Sources & evidence

ORD record: ord-20794454fef14df291ca8b3a6709ed83
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586607B2

Linked notes

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