2-Propenoic acid, (1S)-1-[(phenylmethoxy)methyl]-2-propen-1-yl ester → 2(5H)-Furanone, 5-[(phenylmethoxy)methyl]-, (5S)-

HRID 896830Notes

Reaction equation

HRID 896830 reaction equation
[C:1]([O:5][C@@H:6]([CH:16]=[CH2:17])[CH2:7][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:4])C=C>C(Cl)Cl.Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1>[CH2:9]([O:8][CH2:7][C@H:6]1[O:5][C:1](=[O:4])[CH:17]=[CH:16]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 1

HCID 113682652-Propenoic acid, (1S)-1-[(phenylmethoxy)methyl]-2-propen-1-yl ester

Product 1

HCID 103528582(5H)-Furanone, 5-[(phenylmethoxy)methyl]-, (5S)-Yield 98.5%

Reagents, catalysts & solvents 2

HCID 178425456HCID 178425456, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of acrylate (12) (1.87 g, 8.05 mmol) in CH2Cl2 (700 mL) was added second generation Grubbs' catalyst (4 mol %, 170 mg, 0.322 mmol). The reaction mixture was refluxed for 5 hours, and the solvent then was removed under reduced pressure. Column chromatography on silica gel (30% EtOAc in hexanes as the eluent) yielded the furanone (13) (1.62 g, 98%) as a brown oil, Rf=0.15 (30% EtOAc in hexanes), [α]25D −81.3° (c 1.09, MeOH); 1H-NMR (500 MHz, CDCl3) δ: 3.66 (dd, 1H, J=5.0, 5.5 Hz), 3.71 (dd, 1H, J=5.0, 5.2 Hz), 4.57 (s, 2H), 5.17 (m, 1H), 6.16 (dd, 1H, J=1.9, 3.8 Hz), 7.29-7.37 (m, 5H), 7.48 (dd, 1H, J=1.4, 4.3 Hz); 13C-NMR (125.8 MHz, CDCl3) δ: a 69.86, 74.18, 82.61, 123.03, 128.42, 128.95, 137.69, 154.32, 173.19.

Workup

  1. temperatureThe reaction mixture was refluxed for 5 hours
  2. customthe solvent then was removed under reduced pressure

Sources & evidence

ORD record
ord-cc723e9131914f6da12c878804f50046
Source dataset
uspto-grants-2005_07
Patent number
US06919465B2

Reaction notes

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