Triethylamine → (E)-tert-butyl 3-(4-((6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylate

HRID 632628Notes

Reaction equation

Br[C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[C:8]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:9]=3[S:10][CH:11]=2)=[CH:4][CH:3]=1.[C:20]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])(=[O:23])[CH:21]=[CH2:22].C(N(CC)CC)C>CN(C=O)C.C(Cl)Cl.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:8]2[C:7]([O:6][C:5]3[CH:18]=[CH:19][C:2](/[CH:22]=[CH:21]/[C:20]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:3][CH:4]=3)=[CH:11][S:10][C:9]=2[CH:12]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a microwave vial, 3-(4-bromophenoxy)-6-methoxybenzo[b]thiophene (4 g, 11.93 mmol), tert-butyl acrylate (10.49 mL, 71.6 mmol), and Pd(PPh3)2Cl2 (1.256 g, 1.79 mmol) were suspended in DMF (12 mL) and triethylamine (8.32 mL, 59.7 mmol). The reaction was heated for 60 min at 120° C. under microwave irradiation. The reaction mixture was diluted with DCM and water. The organic layer was collected (phase separator) and concentrated to obtain the crude product. The crude material was purified by column chromatography (SiO2, 1-20% EtOAc/Heptane) to afford (E)-ter-butyl 3-(4-((6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylate (3 g, 7.84 mmol, 66% yield) as a white solid. 1H NMR (CDCl3) δ ppm=7.45-7.63 (m, 4 H), 7.27-7.33 (m, 1 H), 7.03-7.13 (m, 2 H), 6.99 (dd, J=8.8, 2.3 Hz, 1 H), 6.66 (s, 1 H), 6.30 (d, J=16.2 Hz, 1 H), 3.90 (s, 3 H), 1.55 (s, 9 H).

Workup

customThe organic layer was collected (phase separator)
concentrationconcentrated
customto obtain the crude product
customThe crude material was purified by column chromatography (SiO2, 1-20% EtOAc/Heptane)

Sources & evidence

ORD record: ord-2991c8c04e404bedb927118149ac6679
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321746B2

Reaction notes

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