Hydrochloric Acid → HCID 67966831, compound

Temperature

50 °C

To a solution of 1a-methyl-7-{[(methyloxy)methyl]oxy}-1,1a,2,7b-tetrahydrocyclopropa[c]chromene (Intermediate 124, 280 mg) in methanol (16 ml) a 2.0 M aqueous solution of HCl (1.271 ml, 2.54 mmol) was added. The reaction mixture was stirred at 50° C. for 2 hours and then at room temperature overnight at which time the reaction still showed some unreacted starting material, therefore more 2.0 M HCl was added (2 eq.) and stirring was continued at 50° C. for 2 hours. The reaction mixture was then quenched with water and diluted and extracted with dichloromethane, washed with brine, dried over sodium sulphate, filtered and concentrated under vacuum. The residue obtained was purified by silica gel chromatography (Companion system, with a gradient from pure cyclohexane to cyclohexane/ethyl acetate 5/1) to give the title compound as a white solid (192 mg).

1. customat room temperature overnight at which time the reaction
2. stirringstirring
3. waitwas continued at 50° C. for 2 hours
4. customThe reaction mixture was then quenched with water
5. additiondiluted
6. extractionextracted with dichloromethane
7. washwashed with brine
8. dry with materialdried over sodium sulphate
9. filtrationfiltered
10. concentrationconcentrated under vacuum
11. customThe residue obtained
12. customwas purified by silica gel chromatography (Companion system

ORD record

ord-97a1dee8ac5f408f8f0f208422bf9d32

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09346790B2