Hydrochloric Acid → HCID 57771614, compound

To a solution of 8-(1-methoxymethylidene)-5,5-dimethyl-spiro[5.5]undec-1-ene (240 mg) obtained in Step 6 in acetonitrile (6 mL) was added 1N aqueous hydrochloric acid solution (1.1 mL), followed by stirring the reaction mixture at room temperature for 3 hours. Then, after addition of saturated brine, the reaction mixture was extracted with diethyl ether. The organic layer was washed with water, dried and concentrated. The resulting residue was dissolved in a mixed solution of methanol (5.4 mL)-water (0.6 mL). To the solution was added potassium carbonate (150 mg), followed by stirring the reaction mixture at room temperature for 2 hours. Then, after addition of water, the reaction mixture was extracted with diethyl ether. The organic layer was washed with water, dried and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate (volume ratio)=40:1) to give 11,11-dimethyl-spiro[5.5]undec-7-ene-2-carbaldehyde (195 mg).

1. extractionthe reaction mixture was extracted with diethyl ether
2. washThe organic layer was washed with water
3. customdried
4. concentrationconcentrated
5. dissolutionThe resulting residue was dissolved in a mixed solution of methanol (5.4 mL)-water (0.6 mL)
6. additionTo the solution was added potassium carbonate (150 mg)
7. stirringby stirring the reaction mixture at room temperature for 2 hours
8. additionThen, after addition of water
9. extractionthe reaction mixture was extracted with diethyl ether
10. washThe organic layer was washed with water
11. customdried
12. concentrationconcentrated
13. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate (volume ratio)=40:1)

ORD record

ord-cb4e275875ec40c89a09503fa0c6f128

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299296B2