Acetic Acid → 3-(2-Methoxy-2-phenylacetyl)dihydro-2H-pyran-4(3H)-one
Reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[O:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1.N1([C:23](=[O:33])[CH:24]([O:31][CH3:32])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)C=CN=C1.C(O)(=O)C>C1(C)C=CC=CC=1.O>[CH3:32][O:31][CH:24]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:23]([CH:13]1[C:14](=[O:17])[CH2:15][CH2:16][O:11][CH2:12]1)=[O:33]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Lithium bis(trimethylsilyl)amide (2.024 mL, 10.78 mmol) was added to a stirred solution of tetrahydro-4H-pyran-4-one (0.948 mL, 10.27 mmol) in toluene (3 mL) at 0° C. After 2 minutes 1-(1H-imidazol-1-yl)-2-methoxy-2-phenylethanone (1.110 g, 5.13 mmol) was added and the mixture was stirred at 0° C. for 5 minutes. The reaction was quenched with acetic acid (0.882 mL, 15.40 mmol) in 5 mL water. The organic layer was separated and concentrated. The crude product was purified by silica flash chromatography using ethyl acetate (0 to 40%) in heptane giving 3-(2-methoxy-2-phenylacetyl)dihydro-2H-pyran-4(3H)-one (0.245 g, 19%). MS (ES−) m/z 247 (M−H)−
Workup
- customThe organic layer was separated
- concentrationconcentrated
- customThe crude product was purified by silica flash chromatography
Sources & evidence
- ORD record
- ord-d0bfa1fda5e44dae893854255687cb0d
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08188101B2
Reaction notes
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