Sodium Bicarbonate → 4-Oxo-1-(tetrahydro-2H-pyran-4-yl)cyclohexanecarbonitrile
Reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2([C:17]#[N:18])[CH2:16][CH2:15][C:10]3(OCC[O:11]3)[CH2:9][CH2:8]2)[CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+]>C(O)(=O)C.O.[Cl-].[Na+].O>[O:11]=[C:10]1[CH2:15][CH2:16][C:7]([CH:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)([C:17]#[N:18])[CH2:8][CH2:9]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 100 °C
Procedure
A solution of 10.3 g (40.8 mmol) of 8-(tetrahydropyran-4-yl)-1,4-dioxa-spiro[4.5]decane-8-carbonitrile (5) in a mixture of 90 mL of acetic acid and 18 mL of water was heated at 100° C. for 24 h. The mixture was cooled to room temperature and slowly poured onto 1.2 L of cold saturated aqueous sodium bicarbonate solution. The mixture was diluted with 600 mL of brine and extracted six times with methyl-tert-butyl ether. The combined organic phases were washed with water and brine, dried over magnesium sulphate, filtered and concentrated in vacuo. The residue was lyophilized from acetonitrile and water, taken up in water and lyophilized again to give 5.95 g of the ketone, which was used directly in the next step. Rt=0.82 min (Method O). Detected mass: 208.1 (M+H+).
Workup
- temperatureThe mixture was cooled to room temperature
- extractionextracted six times with methyl-tert-butyl ether
- washThe combined organic phases were washed with water and brine
- dry with materialdried over magnesium sulphate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-1591b97b721341febfc04ee79fd2016f
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399482B2
Reaction notes
Loading…