[OH:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[CH2:5][CH2:4]1.[H-].[Na+].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>O1CCCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH2:11]([O:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[CH2:5][CH2:4]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1
To a solution of (R)-5-hydroxymethyl-dihydro-furan-2-one (5 g, 43.06 mmol) in tetrahydrofuran (130 mL) is added sodium hydride (2.58 g, 60% oil dispersion, 64.59 mmol) and tetrabutylammonium iodide (spatula) and stirred for 30 min. To the mixture is added benzyl bromide (6.18 mL, 51.67 mmol) and refluxed for 3 h. The mixture is cooled and diluted with ethyl acetate (150 mL), washed with a saturated solution of ammonium chloride (150 mL) and brine. The mixture is dried over magnesium sulfate, filtered and concentrated in vacuo to yield the title compound, 8.87 g (100%), as a pale yellow oil.
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