Diisobutylaluminumhydride → HCID 21835191, compound

To a solution of ethyl 2-(2,6-dichlorophenyl)propanoate (0.66 g, 2.7 mmol) in THF (30 ml) at 0° C. was added diisobutylaluminium hydride (6.6 ml of a 1.0M solution in THF, 6.6 mmol) dropwise. The cooling bath was removed and the mixture stirred at room temperature for 45 min. More diisobutylaluminium hydride (3 ml of a 1.0M solution in THF, 3.0 mmol) was added and the solution stirred for a further 45 min. After this time more diisobutylaluminium hydride (3 ml of a 1.0M solution in THF, 3.0 mmol) was added and the solution stirred for 1 h. NH4Cl (sat., 10 ml) was added and the mixture stirred at room temperature for 1 h. The organic layer was decanted off and the gelatinous precipitate partitioned between ether (30 ml) and 1M HCl (30 ml). The organic layers were combined, dried (Na2SO4) and evaporated. The residue was chromatographed on silica, eluting with petrol:EtOAc (3:1), to afford the alcohol (546 mg, 100%) as a colourless oil. 1H NMR (250 MHz, CDCl3) δ 1.41 (3H, d, J=6.7 Hz), 3.94-4.01 (2H, m), 4.13-4.23 (1H, m), 7.08 (1H, t, J=7.9 Hz), 7.20-7.40 (2H, m).

1. customThe cooling bath was removed
2. additionMore diisobutylaluminium hydride (3 ml of a 1.0M solution in THF, 3.0 mmol) was added
3. stirringthe solution stirred for a further 45 min
4. additionAfter this time more diisobutylaluminium hydride (3 ml of a 1.0M solution in THF, 3.0 mmol) was added
5. stirringthe solution stirred for 1 h
6. additionNH4Cl (sat., 10 ml) was added
7. stirringthe mixture stirred at room temperature for 1 h
8. customThe organic layer was decanted off
9. customthe gelatinous precipitate partitioned between ether (30 ml) and 1M HCl (30 ml)
10. dry with materialdried (Na2SO4)
11. customevaporated
12. customThe residue was chromatographed on silica
13. washeluting with petrol:EtOAc (3:1)

ORD record

ord-fca31333bdca486282554678b6248385

Source dataset

uspto-grants-1999_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05973156