ChemicalBook CAS DataBase List METHYL (R)-3-PHENYLBUTYRATE

METHYL (R)-3-PHENYLBUTYRATE synthesis

9synthesis methods

Product Name:METHYL (R)-3-PHENYLBUTYRATE
CAS Number:1472-07-7
Molecular formula:C11H14O2
Molecular Weight:178.23

2-Butenoic acid, 3-phenyl-, methyl ester, (E)-

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1472-07-7
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Benzenepropanoic acid, β-methyl-, methyl ester, (βS)-

1441-20-9
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Yield:-

Reaction Conditions:

with [CuF(PPh₃)3]*2MeOH;(Sc,Rp,Ra)-PPFAPhos in tetrahydrofuran;butan-1-ol at 20; for 24 h;Inert atmosphere;Sealed tube;optical yield given as %ee;enantioselective reaction;

Steps:

General procedure for Cu-catalyzed asymmetric conjugate reduction of α,β-unsaturated esters

General procedure: Copper salt (0.0125 mmol) and ligand (0.015 mmol) were added into an oven-dried Schlenk tube. Then, dry THF (2.0 mL) was added under nitrogen. The mixture was stirred at room temperature for 30 min to give a solution. Next, PMHS (60 μL, 1.0 mmol) was added to the reaction mixture and stirred for 30 min. The substrate (0.25 mmol) was then added, followed by t-BuOH (95 μL, 1.0 mmol). The reaction was sealed, and stirred for 24 h. The reaction mixture was quenched with saturated aqueous ammonium chloride solution and the aqueous layer was extracted with Et₂O (3 × 10 mL). The combined organic layers were washed with brine, dried over Na₂SO₄, and concentrated. The product was purified by chromatography on silica gel.

References:

Hou, Chuan-Jin;Guo, Wei-Lei;Hu, Xiang-Ping;Deng, Jun;Zheng, Zhuo [Tetrahedron Asymmetry,2011,vol. 22,# 2,p. 195 - 199] Location in patent:experimental part

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1472-07-7
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References

623-43-8 Synthesis