Ethyl Acetate → HCID 86642024, compound

Tetrahydrofuran (600 mL) was charged to 2 L flask fitted with condenser, nitrogen, thermocouple and mechanical stirrer. The flask was cooled to <10° C. and the flask was inerted with dry nitrogen fed a slow rate. Aluminium chloride (112 g, 840 mmol) was slowly added to the reaction flask whilst maintaining a temperature of <10° C. Then lithium aluminium hydride powder (15.9 g, 420 mmol) was added slowly over 30 minutes. The reaction mixture was stirred for a further 30 minutes at <10° C. To the reaction flask was added slowly a solution of 2-methyl-2-(4-methylpentyl)-1,3-dioxolane (72 g, 420 mmol) in tetrahydrofuran (50 mL) over 30 minutes. The reaction mixtures as stirred for 2 hours at <10° C. Ethyl acetate (200 g) was then added slowly to the reaction mixture to neutralise the excess lithium aluminium hydride—cooling was necessary to counteract the large exotherm. The crude reaction mixture was extracted into methyltert-butyl ether (2×300 mL) and the organic phase washed with water (200 mL). The organic phase was dried over magnesium sulphate, filtered and the solvent removed by evaporation to yield the desired product suitable for the next synthetic step as a colourless oil (100% pure by GC rpa, 70 g, 400 mmol, 96% chemical yield). A small sample was Kugelrohr distilled to give material suitable for olfactive analysis.

1. customfitted with condenser
2. temperatureThe flask was cooled to <10° C.
3. temperaturewhilst maintaining a temperature of <10° C
4. stirringas stirred for 2 hours at <10° C
5. temperaturecooling
6. customThe crude reaction mixture
7. extractionwas extracted into methyltert-butyl ether (2×300 mL)
8. washthe organic phase washed with water (200 mL)
9. dry with materialThe organic phase was dried over magnesium sulphate
10. filtrationfiltered
11. customthe solvent removed by evaporation

ORD record

ord-d585f4bc23f648108be1ba6daa57700a

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08088725B2