Aluminium lithium hydride → 1,5-Anhydro-2,4-dideoxyhexitol

Temperature

0 °C

To a cooled (0° C.), stirred suspension of LiAlH4 (3.42 g, 90.0 mmol) in anhydrous THF (50 mL) was added dropwise a solution of 4-oxo-tetrahydro-pyran-2-carboxylic acid ethyl ester (5.17 g, 30.0 mmol). After stirring for 1 hour, the reaction was quenched by the slow, sequential addition of water (3.4 mL), 15% NaOH (3.4 mL), and water (10.0 mL). The inorganic salt was filtered off and extracted with EtOAc repeatedly since the product was absorbed on the solid. Solvent removal afforded 2.42 g (61%) of yellow oil. The crude mixture was carried to the next step without purification.

1. stirringAfter stirring for 1 hour
2. customthe reaction was quenched by the slow,
3. additionsequential addition of water (3.4 mL), 15% NaOH (3.4 mL), and water (10.0 mL)
4. filtrationThe inorganic salt was filtered off
5. extractionextracted with EtOAc repeatedly since the product
6. customwas absorbed on the solid
7. customSolvent removal

ORD record

ord-8c329ec1b8b44b8c8a1b26e650ded132

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06541481B2