3-Methyl-3-(5-methyl-furan-2-yl)-butyric acid methyl ester → 3-Methyl-3-(5-methyl-furan-2-yl)-butan-1-ol
Reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]([CH3:13])([C:7]1[O:8][C:9]([CH3:12])=[CH:10][CH:11]=1)[CH3:6].[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[CH3:13][C:5]([C:7]1[O:8][C:9]([CH3:12])=[CH:10][CH:11]=1)([CH3:6])[CH2:4][CH2:3][OH:2]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
Step D To a solution of 3-methyl-3-(5-methyl-furan-2-yl)-butyric acid methyl ester (1.5 g, 7.8 mmol) in anhydrous tetrahydrofuran (50 mL) at 0° C. was added a tetrahydrofuran solution (1 M) of LiAlH4 (10 mL, 10 mmol) under nitrogen. The reaction mixture was stirred at 0° C. for 1 h, then poured into a ice-water. The mixture was extracted with ethyl acetate. The organic layer were separated, washed with water, aqueous HCl solution, brine, dried over MgSO4, and concentrated to give 3-methyl-3-(5-methyl-furan-2-yl)-butan-1-ol as a yellow oil (1.2 g, 77%).
Workup
- extractionThe mixture was extracted with ethyl acetate
- customThe organic layer were separated
- washwashed with water, aqueous HCl solution, brine
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c8ef4063fadc4bba819f15fdfb1f6086
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08354444B2
Reaction notes
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