Lithium amide → 2H-Pyran, tetrahydro-2-(9-tetradecyn-1-yloxy)-

A mixture of 7.4 g of compound IV, 1.0 g lithium amide, and 50 ml of dry, purified dioxane was stirred and refluxed 3.5 hours under nitrogen, cooled, 4.5 g of n-butyl bromide was added dropwise and the refluxing and stirring continued for 20 hours more. The mixture was chilled in an icebath, diluted with 60 ml of water and the layers separated. The aqueous layer was extracted three times with ether, the combined organic phase was washed three times with saturated NaCl solution, the solvents were evaporated and the residue distilled to give 3.2 g (36%) of compound V which boiled at 120°-123° (0.03 mm), ND25 1.4634.

1. customof dry
2. custompurified dioxane
3. temperaturerefluxed 3.5 hours under nitrogen
4. temperaturecooled
5. addition4.5 g of n-butyl bromide was added dropwise
6. stirringthe refluxing and stirring
7. temperatureThe mixture was chilled in an icebath
8. additiondiluted with 60 ml of water
9. customthe layers separated
10. extractionThe aqueous layer was extracted three times with ether
11. washthe combined organic phase was washed three times with saturated NaCl solution
12. customthe solvents were evaporated
13. distillationthe residue distilled

ORD record

ord-86a65d602ea649909e781ce6fdc43a7f

Source dataset

uspto-grants-1978_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04083995