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Chemical Structure| 188945-44-0 Chemical Structure| 188945-44-0

Structure of 188945-44-0

Chemical Structure| 188945-44-0

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Product Details of [ 188945-44-0 ]

CAS No. :188945-44-0
Formula : C22H29O5P
M.W : 404.44
SMILES Code : O=C(OCC)CP(OC1=CC=CC=C1C(C)C)(OC2=CC=CC=C2C(C)C)=O

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Application In Synthesis of [ 188945-44-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 188945-44-0 ]

[ 188945-44-0 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 54221-96-4 ]
  • [ 188945-44-0 ]
  • [ 1499179-60-0 ]
YieldReaction ConditionsOperation in experiment
83% General procedure: Triton B (40percent in MeOH, 7.30 mL, 17.5 mmol) was added dropwise to a solution of ethyl 2-[bis(2-isopropylphenoxy) phosphoryl]acetate (5.30 g, 13.1 mmol) in THF (150 mL) at -78 C under Ar. After 15 min of stirring, a solution of 2-methylbenzaldehyde (59) (1.50 g, 12.5 mmol) in THF (50 mL) was added dropwise to the solution. After 10 h of stirring, the mixture was quenched with satd. aq. NH4Cl (30 mL) and extracted with EtOAc (3 x 30 mL). The organic layer was washed successively with H2O, satd. aq. (20 mL) NaHCO3 (20 mL) and brine (20 mL), then dried (MgSO4), filtered and concentratedin vacuo; Z-selective olefination of 6-methoxypicolinaldehyde (112) wasperformed using the procedure described above to provide (Z)-ethyl 3-(6-methoxypyridin-2-yl)acrylate (cis-168) (83percent,Z:E = 99:1, determined by 1H-NMR spectrum) (silica gel CC,EtOAc/hexane, 3:97) as a colorless oil: 1H-NMR (CDCl3, 400 MHz)d: 1.27 (t, J = 7.2 Hz, 3H, ?CH3), 3.89 (s, 3H, ?OCH3), 4.24 (q,J = 7.2 Hz, 2H, ?CH2?), 6.35 (d, J = 12.8 Hz, 1H, CH-CO2?), 6.66(d, J = 8.4 Hz, 1H, Py?H), 6.72 (d, J = 12.8 Hz, 1H, Ar?CH), 7.05(d, J = 7.2 Hz, 1H, Py?H), 7.54 (t, J = 7.2, 8.4 Hz, 1H, Py?H).
  • 2
  • [ 75792-33-5 ]
  • [ 188945-44-0 ]
  • [ 1499179-39-3 ]
YieldReaction ConditionsOperation in experiment
82% General procedure: Triton B (40% in MeOH, 7.30 mL, 17.5 mmol) was added dropwise to a solution of ethyl 2-[bis(2-isopropylphenoxy) phosphoryl]acetate (5.30 g, 13.1 mmol) in THF (150 mL) at -78 C under Ar. After 15 min of stirring, a solution of 2-methylbenzaldehyde (59) (1.50 g, 12.5 mmol) in THF (50 mL) was added dropwise to the solution. After 10 h of stirring, the mixture was quenched with satd. aq. NH4Cl (30 mL) and extracted with EtOAc (3 x 30 mL). The organic layer was washed successively with H2O, satd. aq. (20 mL) NaHCO3 (20 mL) and brine (20 mL), then dried (MgSO4), filtered and concentratedin vacuo.; Z-selective olefination of 76 was performed using the proceduredescribed above to provide (Z)-ethyl 3-(3-isopropoxyphenyl)acrylate(cis-132) (82%, Z:E = 96:4, determined by 1H-NMR spectrum)(silica gel CC, EtOAc/hexane, 10:90) as a colorless oil: 1H-NMR(CDCl3, 400 MHz) d: 1.25 (t, J = 7.2 Hz, 3H, -CH3), 1.34 (d,J = 5.6 Hz, 6H, -CH-(CH3)2), 4.18 (q, J = 7.2 Hz, 2H, -CH2-), 4.56(heptet, J = 5.6 Hz, -CH-(CH3)2), 5.93 (d, J = 12.8 Hz, 1H, CH-CO2-), 6.85 (m, 1H, Ar-H), 6.89 (d, J = 12.8 Hz, 1H, Ar-CH), 7.10(d, J = 7.6 Hz, 1H, Ar-H), 7.22 (s, 1H, Ar-H), 7.25 (d, J = 8.4 Hz, 1H,Ar-H).
 

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