2-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1) → HCID 11528683, compound

Temperature

-20 °C

To a solution of 100.0 g (RS)-2-{[(S)-2-Methylpent-4-in-1-yl]oxy}3,4,5,6-tetrahydro-2H-pyran (Ireland, Robert E. et al., Tetrahedron, 1997, 53, 39, 13221-13256) in 200 ml THF were added, dropwise at −30° C., 439 ml n-butyllithium (15% in hexane). The solution was stirred for 20 minutes at −30° C. and 20 minutes at −20° C. After cooling to −30° C., a solution of 95.6 g N,N-dimethylacetamide in 200 ml THF was added during 15 minutes and the reaction mixture was stirred for 30 minutes at −20°. The reaction mixture was then poured into a stirred precooled (0° C.) mixture of 1000 ml hexane and a solution of 104,8 g citric acid monohydrate in 700 ml water. The aqueous phase was separated and the organic phase was washed with 300 ml water and then filtered over 100 g silica gel. The silica gel was washed with 1000 ml hexane. The combined eluates were reduced to an oil by vacuum distillation.

1. temperatureAfter cooling to −30° C.
2. stirringthe reaction mixture was stirred for 30 minutes at −20°
3. customThe aqueous phase was separated
4. washthe organic phase was washed with 300 ml water
5. filtrationfiltered over 100 g silica gel
6. washThe silica gel was washed with 1000 ml hexane
7. distillationThe combined eluates were reduced to an oil by vacuum distillation

ORD record

ord-a59cf62955874b56b1d88ec17d687bfe

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07326798B2