p-Toluenesulfonic acid → HCID 57182315, compound
Reaction equation
[CH3:1][O:2][C:3]([O:6][CH3:7])([CH3:5])[CH3:4].[C:8]1([CH3:18])[CH:13]=[CH:12][C:11](S(O)(=O)=O)=[CH:10][CH:9]=1.Cl[CH2:20]Cl>>[CH3:4][C:3]1([CH3:5])[O:6][CH2:7][C:10](=[CH2:9])[C@@H:11]2[C@@H:20]([C@@H:8]([CH3:18])[CH2:13][CH2:12]2)[CH2:1][O:2]1Participants
Procedure
2-[(1S, 2R, 3S)-2-(hydroxymethyl)-3-methylcyclopent-1-yl]-2-propen-1-ol (1.5 g, 0.0082 mol) obtained in Definite Example 46 was dissolved in 20 ml of dichloromethane and 10 ml of 2, 2-dimethoxypropane was added. Furthermore, 50 mg of p-toluenesulfonic acid was added, and the reaction mixture was stirred at room temperature for 24 hours. After 100 ml of dichloromethane was added, washing was carried out with a mixed aqueous solution of saturated sodium bicarbonate solution (20 ml) and saturated sodium chloride solution (20 ml), and this organic layer was dried by adding magnesium sulfate, and was filtered and then concentrated under a reduced pressure. The residual matter was purified by chromatography using silica gel, and the solvent of the fraction obtained from hexane:ether=8:2 eluent was distilled off. A colorless oily substance was thus obtained, i.e., (1R, 8S, 11S)-4,4,11-trimethyl-7-methylene-3,5-dioxabicyclo[6.3.0]undecane (550 mg, yield=29.7%). This (1R, 8S, 11S)-4,4,11-trimethyl-7-methylene-3, 5-dioxabicyclo[6.3.0]undecane had the following physicochemical properties:
Workup
- washwashing
- customthis organic layer was dried
- additionby adding magnesium sulfate
- filtrationwas filtered
- concentrationconcentrated under a reduced pressure
- customThe residual matter was purified by chromatography
- customthe solvent of the fraction obtained from hexane
- distillationether=8:2 eluent was distilled off
- customA colorless oily substance was thus obtained
Sources & evidence
- ORD record
- ord-d3819922398c492fb1653dc9ed5027f6
- Source dataset
- uspto-grants-1994_12
- Patent number
- US05374653
Reaction notes
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