(E)-3-(4-Methoxy-phenyl)-but-2-enoic acid ethyl ester → 61292-83-9

HRID 1014763Notes

Reaction equation

HRID 1014763 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:16])=[CH:10][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]([CH:9]([CH3:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 111327(E)-3-(4-Methoxy-phenyl)-but-2-enoic acid ethyl ester

Product 1

HCID 1252740061292-83-9Yield 100.4%

Reagents, catalysts & solvents 2

HCID 23924IridiumCatalystHCID 6344DichloromethaneSolvent

Procedure

According to the general procedure, a solution of ethyl 3-(4-methoxyphenyl)but-2-enoate (58 mg, 0.26 mmol) and iridium catalyst (S)-32 (8.4 mg, 0.0053 mmol, 2 mol %) in CH2Cl2 (3 mL) was hydrogenated. Removal of the solvent in vacuo and standard purification gave 35 (58 mg, 99%) as a colorless oil; [α]20D −26.7 (c 1.00, CHCl3); CSP HPLC analysis (Chiralcel OB-H; eluent: 99.5:0.5 hexanes/i-PrOH, 0.5 mL/min) determined a 96:4 er (92% ee) [tR(major) 21.73 min, tR(minor) 28.91 min]; 1H NMR (300 MHz, CDCl3) 7.14 (d, 2H, J=8.4 Hz), 6.84 (d, 2H, J=8.7 Hz), 4.07 (q, 2H, J=6.9 Hz), 3.78 (s, 3H), 3.24 (sextet, 1H, J=7.2 Hz), 2.61-2.46 (m, 2H), 1.27 (d, 3H, J=6.9 Hz), 1.18 (t, 3H, J=7.2 Hz) ppm; 13C NMR (75 MHz, CDCl3) 172.4, 158.0, 137.8, 131.4, 127.6, 113.8, 60.1, 55.1, 43.2, 35.7, 21.9, 14.1 ppm.

Workup

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

Sources & evidence

ORD record
ord-8ece1cc29c66469db842fe0597435895
Source dataset
uspto-grants-2011_07
Patent number
US07982064B2

Reaction notes

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