Ethyl 2-methyl-3-phenyl-2-propenoate → Ethyl 2-methyl-3-phenylpropanoate

HRID 1014764Notes

Reaction equation

HRID 1014764 reaction equation
[CH3:1][C:2](=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]>[Ir].C(Cl)Cl>[CH3:1][CH:2]([CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

4

Reactant 1

HCID 235357Ethyl 2-methyl-3-phenyl-2-propenoate

Product 1

HCID 562367Ethyl 2-methyl-3-phenylpropanoateYield 88%

Reagents, catalysts & solvents 2

HCID 23924IridiumCatalystHCID 6344DichloromethaneSolvent

Procedure

According to the general procedure, a solution of ethyl 2-methyl-3-phenylacrylate (34 mg, 0.18 mmol) and iridium catalyst (S)-32 (5.7 mg, 0.0036 mmol, 2.0 mol %) in CH2Cl2 (1.8 mL) was hydrogenated. Removal of the solvent in vacuo and standard purification gave 36 (30 mg, 88%) as a colorless oil. [α]20D +28.4 (c 1.0, CHCl3); CSP HPLC analysis (Chiralcel OB-H; eluent: 99.5:0.5 hexanes/i-PrOH, 0.5 mL/min) determined a 91:9 er (82% ee) [tR(minor) 8.52 min, tR(major) 10.10 min]; 1H NMR (300 MHz, CDCl3) 7.31-7.16 (m, 5H), 4.09 (q, 2H, J=6.9 Hz), 3.08-2.98 (m, 1H), 2.79-2.64 (m, 2H), 1.21 (d, 3H, J=7.2 Hz), 1.16 (d, 3H, J=6.3 Hz) ppm; 13C NMR (75 MHz, CDCl3) 176.1, 139.4, 128.9, 128.3, 126.2, 60.2, 41.4, 39.7, 16.7, 14.1 ppm.

Workup

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

Sources & evidence

ORD record
ord-c7517f9230f64c639bf1f78ccb3e6506
Source dataset
uspto-grants-2011_07
Patent number
US07982064B2

Reaction notes

Loading…