Methanol → 4-(Hydroxymethyl)tetrahydro-2H-pyran-4-carbonitrile
Reaction equation
[C:1]([C:3]1([C:9](OC)=[O:10])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)#[N:2].CO.O.[BH4-].[Na+]>O1CCCC1.C(OCC)(=O)C>[C:1]([C:3]1([CH2:9][OH:10])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)#[N:2]Participants
7
Procedure
Methyl 4-cyanotetrahydro-2H-pyran-4-carboxylate (2.93 g, 17.3 mmol) was dissolved in tetrahydrofuran (50 mL), methanol (10 mL) and water (5.0 mL). To this, sodium borohydride (1.31 g, 34.6 mmol) was added and the mixture was stirred at room temperature for 30 minutes. The reaction was stopped by addition of water to the reaction mixture, and extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate) to give 4-cyanotetrahydro-2H-pyran-4-ylmethanol (1.59 g, yield: 92%).
Workup
- washby washing with brine
- dry with materialdrying over anhydrous sodium sulfate
- customThe solvent was evaporated off under reduced pressure
- customthe residue was purified by silica gel column chromatography (ethyl acetate)
Sources & evidence
- ORD record
- ord-e0a4dcaf845e4ea990aabfca7bdeca90
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08673908B2
Reaction notes
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