Tetrahydrofuran → HCID 58016894, compound

Temperature

-78 °C

Add 187.4 ml (187.4 mmol) of a 1 M solution of D113AH in THF dropwise to a solution of 17.87 g (178.5 mmol) (R)-γ-valerolactone [(5R)-5-methyldihydrofuran-2(3H)-one] in 200 ml abs. THF cooled to −78° C. Stir the solution for a further 1 h at −78° C. and then add solution A prepared above. At the end of addition, slowly heat the mixture to RT and stir overnight at RT. Add the reaction mixture to 300 ml ethyl acetate and precipitate with 50 ml concentrated potassium sodium tartrate solution. After phase separation, extract the aqueous phase again with ethyl acetate. Combine the organic phases, wash with satd. sodium chloride solution, dry over magnesium sulphate and concentrate under vacuum. Purify the residue by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 5:1). 32.2 g (90.1% of theor.) of the target product, containing small amounts of the cis-isomer, is obtained.

1. additionAt the end of addition
2. temperatureslowly heat the mixture to RT
3. stirringstir overnight at RT
4. customAfter phase separation
5. extractionextract the aqueous phase again with ethyl acetate
6. washwash with satd
7. dry with materialsodium chloride solution, dry over magnesium sulphate
8. concentrationconcentrate under vacuum
9. customPurify the residue by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 5:1)
10. addition32.2 g (90.1% of theor.) of the target product, containing small amounts of the cis-isomer
11. customis obtained

ORD record

ord-afbe09d458614ef39ade0a2f08c3fcaf

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08183246B2