Water → 2-[4-(4-Ethoxycarbonyl-1-butenyl)phenyl]ethyl alcohol

To a solution of 4-(2-t-butyldimethylsiloxyethyl)bromobenzene (4.29 g) in tetrahydrofuran (30 ml) was added n-butyllithium (1.64 mol/l solution in tetrahydrofuran, 9.0 ml) at -78° C., and the mixture was stirred at the same temperature for 15 minutes. To the reaction mixture was added N,N-dimethylformamide (1.3 ml), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into water, and the mixture was extracted with diethyl ether. The extract was concentrated to dryness under reduced pressure to give 4-(2-t-butyldimethylsiloxyethyl)benzaldehyde(3.59 g)To a solution of ethyl triphenylphosphranylidenebutylate (2.22 g), which was prepared from (3-carboethoxypropyl)triphenylphosphonium bromide and sodium bis(trimethylsilyl)amide, in tetrahydrofuran (25 ml) was added 4-(2-t-butyldimethylsiloxyethyl)benzaldehyde (1.57 g) at -78° C., and the mixture was stirred at the same temperature for 4 hours and allowed to stand at room temperature for 12 hours. The reaction mixture was poured into water, and the mixture was extracted with diethyl ether. The extract was washed with brine, dried over anhydrous MgSO4, and the solvent was removed under reduced pressure. To a solution of the residue in acetonitrile (80 ml) was added a 47% hydrofluoric acid (1 ml), and the mixture was stirred at room temperature for 1 hour. The solvent was concentrated under reduced pressure. The residue was dissolved in chloroform, the solution was washed with a saturated aqueous NaHCO3 solution, and dried over anhydrous MgSO4. The solvent was removed under reduced pressure. The residue was purified by medium pressure liquid column chromatography on a silica gel column using a mixture of methylene chloride, diethyl ether and methanol (1:1:1) as eluent to give 2-[4-(4-ethoxycarbonyl-1-butenyl)phenyl]ethyl alcohol (0.35 g).

1. waitto stand at room temperature for 12 hours
2. extractionthe mixture was extracted with diethyl ether
3. washThe extract was washed with brine
4. dry with materialdried over anhydrous MgSO4
5. customthe solvent was removed under reduced pressure
6. additionTo a solution of the residue in acetonitrile (80 ml) was added a 47% hydrofluoric acid (1 ml)
7. stirringthe mixture was stirred at room temperature for 1 hour
8. concentrationThe solvent was concentrated under reduced pressure
9. dissolutionThe residue was dissolved in chloroform
10. washthe solution was washed with a saturated aqueous NaHCO3 solution
11. dry with materialdried over anhydrous MgSO4
12. customThe solvent was removed under reduced pressure
13. customThe residue was purified by medium pressure liquid column chromatography on a silica gel column
14. additiona mixture of methylene chloride, diethyl ether and methanol (1:1:1) as eluent

ORD record

ord-2bf1bcb01e6d42a9b4f7718294203b4f

Source dataset

uspto-grants-1997_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05624948