(2-Methyl-furan-3-yl)-acetic acid ethyl ester → 2-(2-Methylfuran-3-yl)ethan-1-ol
Reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[CH:10]=[CH:9][O:8][C:7]=1[CH3:11])C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:11][C:7]1[O:8][CH:9]=[CH:10][C:6]=1[CH2:5][CH2:4][OH:3]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of (2-methyl-furan-3-yl)-acetic acid ethyl ester (11.8 g, 70.2 mmoles) in tetrahydrofuran (50 ml) was added to a stirred suspension of lithium aluminium hydride (2.66 g, 70.2 mmoles) under a nitrogen atmosphere and with cooling to 0° C. When the addition was complete the mixture was stirred at room temperature for 3 hours, then quenched by the addition of excess acetone. After acidifying with 10% aqueous hydrochloric acid the mixture was extracted three times with diethyl ether. The combined extracts were dried and evaporated to afford crude 2-(2-methyl-furan-3-yl)-ethanol as a yellow oil. (ii) Compound (70) was prepared in the form of a pale yellow oil from crude 2-(2-methyl-furan-3-yl)-ethanol (from (i)) by adapting the procedure of Example 1(a).
Workup
- additionWhen the addition
- customquenched by the addition of excess acetone
- extractionwas extracted three times with diethyl ether
- customThe combined extracts were dried
- customevaporated
Sources & evidence
- ORD record
- ord-f0d072bfbbd648fd8d53c1bd94449397
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07858644B2
Reaction notes
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