Methyl 1-benzofuran-2-carboxylate → 1-Benzofuran-2-Ylmethanol
Reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10](OC)=[O:11].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[OH:11][CH2:10][C:2]1[O:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
The crude product 3 (324 g) was dissolved in anhydrous ethyl ether. The solution was kept under inert atmosphere (nitrogen or argon) and cooled to 0° C. in an ice bath. A 1M solution of lithium aluminum hydride in ether (620 ml) was added dropwise, while stirring, over a period of 1 hour. The solution was then washed with 2N HCl (4×1,000 ml), with 2N KOH (2×500 ml), and with water (1,000 ml). The material was dried over magnesium sulfate, filtered, and the solvent evaporated. The crude product was distilled in vacuo, yielding approximately 155.36 g (1.05 mol). The boiling point is 110° C. at 1.5 mm Hg.
Workup
- washThe solution was then washed with 2N HCl (4×1,000 ml), with 2N KOH (2×500 ml)
- dry with materialThe material was dried over magnesium sulfate
- filtrationfiltered
- customthe solvent evaporated
- distillationThe crude product was distilled in vacuo
- customyielding approximately 155.36 g (1.05 mol)
Sources & evidence
- ORD record
- ord-aba9cf5ebfce49918129a8f411852367
- Source dataset
- uspto-grants-1994_11
- Patent number
- US05364880
Reaction notes
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