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

HRID 332857
Notes
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Reaction equation

HRID 332857 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 15458tert-Butyl acrylateHCID 867306383-(4-Bromophenoxy)-6-methoxybenzo[b]thiophene

Product 1

HCID 86730640(E)-tert-butyl 3-(4-((6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylateYield 66%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compound
Catalyst
HCID 962WaterSolvent
HCID 6228DimethylformamideSolvent
HCID 6344DichloromethaneSolvent

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)-tert-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, 4H), 7.27-7.33 (m, 1H), 7.03-7.13 (m, 2H), 6.99 (dd, J=8.8, 2.3 Hz, 1H), 6.66 (s, 1H), 6.30 (d, J=16.2 Hz, 1H), 3.90 (s, 3H), 1.55 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-704f0d6e2a09413886bdbbcca0d119d3
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08877801B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes