Hydrochloric Acid → HCID 67593801, compound

Temperature

-78 °C

7-Methoxyisothiochroman-4-one from Step 3 (0.58 g, 3.0 mmol) was dissolved in tetrahydrofuran (30 mL) and cooled to -78° C. A solution of sodium bistrimethylsilylamide (3.0 mL of a 1.0M tetrahydrofuran solution) was added and the reaction stirred for 0.5 hours at -78° C. Trifluoroacetyl imidazole (0.41 mL, 3.6 mmol) was added and the reaction was warmed to room temperature and stirred under a nitrogen atmosphere for 16 hours. At this time, 1N hydrochloric acid (200 mL) was added to the reaction followed by extraction with ether (250 mL). The organics were washed with brine (150 mL), dried over MgSO4 and concentrated in vacuo. The resulting yellow oil (0.42 g, 48%) was used without further purification.

1. temperaturethe reaction was warmed to room temperature
2. stirringstirred under a nitrogen atmosphere for 16 hours
3. extractionfollowed by extraction with ether (250 mL)
4. washThe organics were washed with brine (150 mL)
5. dry with materialdried over MgSO4
6. concentrationconcentrated in vacuo
7. customThe resulting yellow oil (0.42 g, 48%) was used without further purification

ORD record

ord-535d7ced92f240aeaa55ce919b9e359f

Source dataset

uspto-grants-1996_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05565482