Water → 3-((9Z,12Z)-octadeca-9,12-dienyloxy)dihydrofuran-2(3H)-one
Reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][O:5][C:3]1=[O:4].CS(O[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[CH2:13]([O:1][CH:2]1[CH2:7][CH2:6][O:5][C:3]1=[O:4])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]Participants
6
Conditions
- Temperature
- 80 °C
Procedure
To a solution of α-hydroxybutyrolactone (2.0 g, 19.6 mmol) and linoleyl methane sulfonate (5.4 g, 15.7 mmol) in anhydrous DMF (60 mL), was added cesium carbonate (8.0 g, 24.5 mmol). The solution was stirred overnight under nitrogen at 80° C. Upon completion, the reaction was poured into water (100 mL) and extracted with ethyl acetate (3×100 mL). The combined ethyl acetate extracts were washed with brine (3×50 mL), dried on magnesium sulfate, filtered and concentrated in vacuo to dryness. The residue was purified by column chromatography on silica gel 60 (eluted with 10% ethyl acetate in hexanes) to afford 3-((9Z,12Z)-octadeca-9,12-dienyloxy)dihydrofuran-2(3H)-one as a pale yellow oil (3.5 g, 51%).
Workup
- extractionextracted with ethyl acetate (3×100 mL)
- washThe combined ethyl acetate extracts were washed with brine (3×50 mL)
- customdried on magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo to dryness
- customThe residue was purified by column chromatography on silica gel 60 (eluted with 10% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-97b79ea0ef2b4af58496f2db07934373
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08466122B2
Reaction notes
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