Dimethylformamide → (3-Ethylphenyl)methanol

Temperature

-78 °C

n-Butyllithium (34 ml of a 2.5M solution in hexanes) was added to a solution of 1-bromo-3-ethylbenzene (15 g) in tetrahydrofuran (320 ml) at −78° C. After 1 hour N,N-dimethylformamide (15 ml) was added. The mixture was stirred at −78° C. for 1 hour and allowed to warm to room temperature. The mixture was quenched with aqueous ammonium chloride and partitioned between ethyl acetate and water. The organic phase was dried (MgSO4) and evaporated. The residue was dissolved in methanol (250 ml) and treated with sodium borohydride (1.51 g) portionwise. The mixture was stirred at room temperature for 16 hours, quenched with 2M HCl (100 ml) and stirred for 4 hours. The mixture was concentrated under reduced pressure and the residue partitioned between ethyl acetate and 2M HCl. The organic phase was dried (MgSO4), evaporated and the residue purified by chromatography eluting with 5-10% ethyl acetate in isohexane.

1. temperatureto warm to room temperature
2. customThe mixture was quenched with aqueous ammonium chloride
3. custompartitioned between ethyl acetate and water
4. dry with materialThe organic phase was dried (MgSO4)
5. customevaporated
6. dissolutionThe residue was dissolved in methanol (250 ml)
7. additiontreated with sodium borohydride (1.51 g) portionwise
8. stirringThe mixture was stirred at room temperature for 16 hours
9. customquenched with 2M HCl (100 ml)
10. stirringstirred for 4 hours
11. concentrationThe mixture was concentrated under reduced pressure
12. customthe residue partitioned between ethyl acetate and 2M HCl
13. dry with materialThe organic phase was dried (MgSO4)
14. customevaporated
15. customthe residue purified by chromatography
16. washeluting with 5-10% ethyl acetate in isohexane

ORD record

ord-7614c6145c424c9396a8ab177d39f1fb

Source dataset

uspto-grants-2001_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06218376B1