Lithium diisobutylaluminum hydride → HCID 59277551, compound

Diisobutylaluminum lithium hydride (30.7 mL of a 1.0 M in hexanes, 30.7 mmol) was added dropwise to an ice-cold solution of 3-chloro-2-propoxybenzoic acid propyl ester (2.63 g, 10.2 mmol) in THF (20 mL). After the addition was complete, the ice bath was removed and the mixture stirred at ambient temperature for 18 h. The reaction was cooled to 0° C. and HCl (1N, 100 mL) was added until all the resulting solids returned to solution. The solution was extracted with Et2O (3×100 mL). The combined organics were washed with brine (2×100 mL), dried (Na2SO4) filtered and concentrated to yield the title compound (1.12 g, 56%) as a light yellow oil: 1H NMR (500 MHz, DMSO-d6) δ 7.40-7.33 (m, 2H), 7.13 (t, J=7.7 Hz, 1H), 5.22 (t, J=5.6 Hz, 1H), 5.56 (d, J=5.6 Hz, 2H), 3.84 (t, J=6.4 Hz, 2H), 1.76-1.71 (m, 2H), 1.01 (t, J=7.3 Hz, 3H).

1. additionAfter the addition
2. customthe ice bath was removed
3. temperatureThe reaction was cooled to 0° C.
4. additionHCl (1N, 100 mL) was added until all the resulting solids
5. extractionThe solution was extracted with Et2O (3×100 mL)
6. washThe combined organics were washed with brine (2×100 mL)
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-4e93f43cdfbb43f481a1c6dd5cf734e3

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07879872B2