Ethyl 3-(4-methoxyphenyl)-2-methylprop-2-enoate → Ethyl 3-(4-methoxyphenyl)-2-methylpropanoate

HRID 1014765Notes

Reaction equation

HRID 1014765 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[C:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1>[Ir].C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 53711494Ethyl 3-(4-methoxyphenyl)-2-methylprop-2-enoate

Product 1

HCID 11160380Ethyl 3-(4-methoxyphenyl)-2-methylpropanoateYield 96.4%

Reagents, catalysts & solvents 2

HCID 23924IridiumCatalystHCID 6344DichloromethaneSolvent

Procedure

According to the general procedure, a solution of ethyl 3-(4-methoxyphenyl)-2-methylacrylate (30 mg, 0.14 mmol) and iridium catalyst (S)-32 (4.5 mg, 0.0029 mmol, 2.0 mol %) in CH2Cl2 (1.4 mL) was hydrogenated. Removal of the solvent in vacuo and standard purification gave 37 (30 mg, 96%) as a colorless oil. [α]20D +24.5 (c 1.25, CHCl3); CSP HPLC analysis (Chiralcel OB-H; eluent: 99.5:0.5 hexanes/i-PrOH, 0.5 mL/min) determined a 90:10 er (80% ee) [tR(minor) 9.01 min, tR(major) 9.76 min]; 1H NMR (300 MHz, CDCl3) 7.08 (d, 2H, J=8.7 Hz), 6.81 (d, 2H, J=8.7 Hz), 4.09 (q, 2H, J=7.2 Hz), 3.78 (s, 3H), 3.01-2.90 (m 1H), 2.73-2.57 (m, 2H), 1.19 (t, 3H, J=7.2 Hz), 1.13 (d, 3H, J=6.6 Hz) ppm; 13C NMR (75 MHz, CDCl3) 176.2, 158.1, 131.4, 129.9, 113.7, 60.2, 55.2, 41.7, 38.8, 16.7, 14.2 ppm.

Workup

  1. customRemoval of the solvent
  2. customin vacuo and standard purification

Sources & evidence

ORD record
ord-8d8eec3572974c5fa9d3a31da4db50e6
Source dataset
uspto-grants-2011_07
Patent number
US07982064B2

Reaction notes

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