Gamma-Butyrolactone → 3-[Hydroxy(3-methoxyphenyl)methyl)-2-oxotetrahydrofuran
Reaction equation
[C:1]1(=[O:6])[O:5][CH2:4][CH2:3][CH2:2]1.[Li].[Li+].CC([N-]C(C)C)C.[CH:16](=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=1>O1CCCC1.C1CCCCC1.O.C(OCC)(=O)C>[OH:25][CH:16]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=1)[CH:2]1[CH2:3][CH2:4][O:5][C:1]1=[O:6]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Procedure
To a solution of γ-butyrolactone (3.0 g) in tetrahydrofuran (THF) (30 ml) was added lithium diisopronylamide (LDA) (28 ml, 1.5 M solution in cyclohexane) at -78° C. under N2, and then after 30 minutes, a solution of m-anisaldehyde (4.7 g) in THF (10 ml) was added in the solution. After being stirred for 2 hours at the same temperature, the solution was poured into the mixture of ethyl acetate and water. The organic layer was washed with 1N-HCl solution, sat. NaHCO3 and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford 3-[hydroxy(3-methoxyphenyl)methyl)-2-oxotetrahydrofuran (7.4 g) MS (m/z): 205 (M+ +17) IR (Neat): 3400, 1725 cm-1NMR (CDCl3, δ): 2.2-2.8 (4H, m), 3.81 (3H, s), 4.1-4.4 (2H, m), 4.80 (1H, d, J=8.0 Hz), 6.8-7.1 (3H, m), 7.27 (1H, t, J=8.0 Hz)
Workup
- washThe organic layer was washed with 1N-HCl solution, sat. NaHCO3 and brine
- dry with materialdried over MgSO4
- customevaporated in vacuo
- customThe residue was purified by chromatography on silica gel
Sources & evidence
- ORD record
- ord-03ed4de8d698427b804ff57ad90523c0
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05972965
Reaction notes
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