Phenylacetylene → HCID 67072655, compound

HRID 2042999Notes

Reaction equation

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

Participants

Reactant 2

HCID 10821Phenylacetylene

HCID 54757833HCID 54757833, compound

Product 1

HCID 67072655HCID 67072655, compound

Procedure

The title compound was prepared from ethynylbenzene (0.05 mL, 0.46 mmol) and trans-2-(4-iodophenyl)cyclopropanecarboxylic acid (100 mg, 0.35 mmol) according to the general procedure IC to give 47 mg (53%) of a white solid after purification by flash chromatography (SiO2, EtOAc:PE, 1:2→1:0): Rt=12.54 min (HPLC method I); 1H NMR (CDCl3) δ 7.53-7.51 (m, 2H), 7.47-7.44 (m, 2H), 7.36-7.31 (m, 3H), 7.09-7.07 (m, 2H), 2.63-2.58 (m, 1H), 1.95-1.90 (m, 1H), 1.72-1.67 (m, 1H), 1.44-1.39 (m, 1H); 13C NMR (CDCl3) δ 179.5, 140.0, 131.9, 131.7, 128.5, 128.4, 126.4, 123.4, 121.8, 89.7, 89.2, 27.1, 24.3, 17.8; ESI-MS calcd for C18H14O2 (M+Na+) 285.0887. found 285.0894.

Sources & evidence

ORD record: ord-b7852b6a561d4922913269c09682f1de
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586607B2

Reaction notes

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