Methanol → 3-(4-Cyanotetrahydro-2H-pyran-4-yl)benzoic acid
Reaction equation
[C:1]([C:3]1([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([O:14]C)=[O:13])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)#[N:2].O.[OH-].[Li+].CO.O>O1CCCC1>[C:1]([C:3]1([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([OH:14])=[O:13])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)#[N:2]Participants
6
Procedure
To a solution of methyl 3-(4-cyanotetrahydro-2H-pyran-4-yl)benzoate (0.62 g, 2.5 mmol) in tetrahydrofuran (6.0 mL) were added lithium hydroxide-monohydrate (0.18 g, 4.3 mmol), methanol (2.0 mL) and water (2.0 mL), and the mixture was stirred at room temperature for 12 hr. The solvent was evaporated under reduced pressure, and the residue was diluted with water (5.0 mL). The mixture was adjusted to pH 3 by slowly adding 1N hydrochloric acid. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and filtrated. The solvent was evaporated under reduced pressure to give the title compound (0.48 g, 83%) as a white powder.
Workup
- customThe solvent was evaporated under reduced pressure
- additionthe residue was diluted with water (5.0 mL)
- additionby slowly adding 1N hydrochloric acid
- extractionThe mixture was extracted with ethyl acetate
- washthe organic layer was washed with water and saturated brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltrated
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-94e9f6322c2641d38758272ad150510c
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273741B2
Reaction notes
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