Acetic Acid → Methyl 5-(1-pyrrolidinylmethyl)-2-furancarboxylate
Reaction equation
[CH:1]([C:3]1[O:7][C:6]([C:8]([OH:10])=[O:9])=[CH:5][CH:4]=1)=O.[N+](=[CH2:13])=[N-].CCOCC.CC(O)=O.[NH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O.CCCCCC>[CH3:13][O:10][C:8]([C:6]1[O:7][C:3]([CH2:1][N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:4][CH:5]=1)=[O:9]Participants
Reactant 7
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 5-formyl-furan-2-carboxylic acid (2 g, 14.3 mmol) in THF (5 ml) at r.t. was treated with freshly prepared diazomethane in ether (ca. 20 mg/ml) (0.72 ml, 1.2 eq.). The solvent was evaporated and the crude product (1 g, 6.5 mmol) dissolved in THF (10 ml). AcOH (467 mg, 7.8 mmol, 1.2 eq.) and pyrrolidine (554 mg, 7.8 mmol, 1.2 eq.) were added and the mixture stirred at r.t. for 5 hrs. Sodium triacetoxyborohydride (2.06 g, 9.7 mmol, 1.5 eq.) was then added and stirring continued at r.t. under Ar overnight. Satd. NaHCO3 (50 ml) was then added and the mixture extracted with EtOAc, dried with Na2SO4 and the solvent evaporated. The residue was chromatographed over 90 g SiO2 (Merck 230-400 mesh) with EtOAc/n-hexane 1:1 affording the title compound (426 mg, 31% yield) as an orange oil. MS: m/e=209 (M+).
Workup
- customThe solvent was evaporated
- stirringstirring
- customcontinued at r.t. under Ar overnight
- extractionthe mixture extracted with EtOAc
- dry with materialdried with Na2SO4
- customthe solvent evaporated
Sources & evidence
- ORD record
- ord-89c228d88b3b4513b617369d54d6b247
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06265426B1
Reaction notes
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