Tetrahydrofuran → Chroman-4-ol

Borane-dimethylsulfide complex (BH3—SMe2) (10 M, 1.14 mL, 11.4 mmol) in THF was added dropwise at 0° C. to a solution of compound 1 (1 g, 2.9 mmol) in THF (12 mL), and the resultant mixture was stirred at 0° C. for 4 hrs. After completion of the reaction, the mixture was quenched with H2O (7 mL), and then continually stirred for 5 min, followed by addition of 10% NaOH (2 mL) and 37% H2O2 (0.36 mL). After stirring for 30 min, the mixture was extracted with CH2Cl2 (30 mL×5). The organic layers were combined and dried with anhydrous MgSO4. After filtration, the filtrate was concentrated in vacuo, followed by purification via silica gel column chromatography (ethyl acetate/n-hexane=1:4), thus giving the title compound 4 as a colorless crystal (0.63 g, 60% yield).

1. customAfter completion of the reaction
2. customthe mixture was quenched with H2O (7 mL)
3. additionfollowed by addition of 10% NaOH (2 mL) and 37% H2O2 (0.36 mL)
4. stirringAfter stirring for 30 min
5. extractionthe mixture was extracted with CH2Cl2 (30 mL×5)
6. dry with materialdried with anhydrous MgSO4
7. filtrationAfter filtration
8. concentrationthe filtrate was concentrated in vacuo
9. customfollowed by purification via silica gel column chromatography (ethyl acetate/n-hexane=1:4)

ORD record

ord-e8910e10b64b4a44978a8b0c7d15733a

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07875735B2