Triacetoxyperiodinane → 2,2-Dimethyl-3-(3-methylcyclohexyl)propanal
Reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:23][C:24]([CH3:35])([CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH:30]([CH3:34])[CH2:29]1)[CH2:25][OH:26]>ClCCl>[CH3:23][C:24]([CH3:35])([CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH:30]([CH3:34])[CH2:29]1)[CH:25]=[O:26]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of Dess Martin periodinane (9.0 g, 21.1 mmol, 1.3 eq) in dichloromethane (165 mL) was charged into a 250 mL three-necked round-bottom flask, equipped with a mechanical stirrer and a reflux condenser. The solution was cooled to 0° C. by the mean of an ice/salt bath. 2,2-dimethyl-3-(3-methylcyclohexyl)propan-1-ol (3.0 g, 16.3 mmol) was added dropwise. After stirring for 2 h at ambient temperature, the mixture was cooled down to −15° C. and the solid was filtered off. The organic solution was then concentrated. The resultant crude product was chromatographed on a silica gel column with 2% EtOAc in hexane as elution agent giving 2,2-dimethyl-3-(3-methylcyclohexyl)propanal (1.0 g, gc purity>85%; yield 33%).
Workup
- customequipped with a mechanical stirrer and a reflux condenser
- temperaturethe mixture was cooled down to −15° C.
- filtrationthe solid was filtered off
- concentrationThe organic solution was then concentrated
- customThe resultant crude product was chromatographed on a silica gel column with 2% EtOAc in hexane as elution agent
Sources & evidence
- ORD record
- ord-47e0ea507ee44889adeeed6b25d52564
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08709994B2
Reaction notes
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