Triphenylphosphine → (E)-methyl 3-(4-((6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)oxy)phenyl)acrylate

HRID 632643Notes

Reaction equation

HRID 632643 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([O:11][C:12]3[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[C:20]([O:22][CH3:23])=[O:21])=[CH:14][CH:13]=3)=[C:9]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[S:8](=O)[C:7]=2[CH:33]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([O:11][C:12]3[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[C:20]([O:22][CH3:23])=[O:21])=[CH:14][CH:13]=3)=[C:9]([C:24]3[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=3)[S:8][C:7]=2[CH:33]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 86730656(E)-methyl 3-(4-((6-methoxy-2-(4-methoxyphenyl)-1-oxidobenzo[b]thiophen-3-yl)oxy)phenyl)acrylate

Product 1

HCID 86730659(E)-methyl 3-(4-((6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)oxy)phenyl)acrylateYield 58.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To a 30 mL vial containing (E)-methyl 3-(4-((6-methoxy-2-(4-methoxyphenyl)-1-oxidobenzo[b]thiophen-3-yl)oxy)phenyl)acrylate (200 mg, 0.43 mmol) was added THF (5 mL), triphenylphosphine (420 mg, 1.60 mmol) and TMS-C1 (0.553 mL, 4.32 mmol). The reaction was heated to 75° C. for 18 h after which time the mixture was cooled to room temperature, quenched with sat. aq. NaHCO3 and diluted with DCM. The organic phase was collected (phase separator) and concentrated in vacuo to afford the crude product which was purified by column chromatography (SiO2, 0-60% EtOAc/Heptane) to afford (E)-methyl 3-(4-((6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)oxy)phenyl)acrylate (110 mg, 0.25 mmol, 57% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm=7.58-7.73 (m, 3 H), 7.38-7.50 (m, J=8.59 Hz, 2 H), 7.28 (t, J=2.27 Hz, 2 H), 6.96-7.05 (m, J=8.59 Hz, 2 H), 6.85-6.96 (m, 3H), 6.32 (d, J=15.66 Hz, 1 H), 3.90 (s, 3 H), 3.81 (s, 3 H), 3.82 (s, 3 H).

Workup

  1. temperaturewas cooled to room temperature
  2. customquenched with sat. aq. NaHCO3
  3. additiondiluted with DCM
  4. customThe organic phase was collected (phase separator)
  5. concentrationconcentrated in vacuo
  6. customto afford the crude product which
  7. customwas purified by column chromatography (SiO2, 0-60% EtOAc/Heptane)

Sources & evidence

ORD record
ord-6b4730ba312e4668a9c7e38cd127e8d6
Source dataset
uspto-grants-2016_04
Patent number
US09321746B2

Reaction notes

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