Ammonia → Methyl tetrahydrofuran-2-carboxylate
Reaction equation
C[C:2]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH2:4][O:3]1.OS(O)(=O)=O.N.[O-]S([O-])(=O)=O.[Na+].[Na+].[CH3:23]O>C1(C)C=CC=CC=1>[O:3]1[CH2:4][CH2:5][CH2:6][CH:2]1[C:7]([O:9][CH3:23])=[O:8]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 95 °C
Procedure
To a mixture of methyl tetrahydrofuran-2-carboxylic acid (11.6 g, 100 mmol), MeOH (20 mL), and toluene (30 mL) was slowly added concentrated H2SO4 (6 g). The resulting biphasic mixture was heated in a sealed pressure vessel for 1 hour at 95° C. The reaction was then cooled to 0° C. and 7N NH3 in MeOH was added until the pH reached between 7 and 9. Na2SO4 was then added, and the reaction was passed through short plug of silica gel, eluting with DCM. The resulting mixture was distilled at 64° C. under vacuum to afford the product as a clear liquid.
Workup
- temperatureThe reaction was then cooled to 0° C.
- washeluting with DCM
- distillationThe resulting mixture was distilled at 64° C. under vacuum
Sources & evidence
- ORD record
- ord-091bac84804c4aebb9640290ac06da41
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07635715B2
Reaction notes
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