Butanal → HCID 23028680, compound

Temperature

-78 °C

In an argon gas stream and at −78° C., n-butyl lithium (a 1.57M hexane solution, 7.01 ml, 11.0 mmol) was added to a tetrahydrofuran (50 ml) solution of the 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (3.03 g, 10.0 mmol) obtained in Example 5 and the mixture was stirred at −78° C. for 1 hour. Butanal (1.08 ml, 12.0 mmol) was added dropwise to the reaction mixture. The mixture was stirred for 15 hours while elevating its temperature to room temperature. After cooling to 0° C. and addition of a saturated aqueous ammonium chloride solution, the mixture was extracted with diethyl ether. The extracts were combined, washed successively with water and brine, dried over MgSO4, and then concentrated. The solid thus precipitated was collected by filtration and washed with hexane. The filtrate and washing with hexane were combined, followed by concentration. The residue was purified by medium-pressure chromatography on a silica gel column (10% ethyl acetate-hexane) as a high-polarity isomer to yield a colorless solid. The resulting colorless solid was recrystallized from hexane, whereby the title compound (396 mg, 11%) was obtained as colorless needle crystals.

1. stirringThe mixture was stirred for 15 hours
2. customto room temperature
3. temperatureAfter cooling to 0° C.
4. extractionthe mixture was extracted with diethyl ether
5. washwashed successively with water and brine
6. dry with materialdried over MgSO4
7. concentrationconcentrated
8. customThe solid thus precipitated
9. filtrationwas collected by filtration
10. washwashed with hexane
11. washThe filtrate and washing with hexane
12. concentrationfollowed by concentration
13. customThe residue was purified by medium-pressure chromatography on a silica gel column (10% ethyl acetate-hexane) as a high-polarity isomer
14. customto yield a colorless solid
15. customThe resulting colorless solid was recrystallized from hexane, whereby the title compound (396 mg, 11%)
16. customwas obtained as colorless needle crystals

ORD record

ord-5d021c0d560b467eae6931bc4e4a9249

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07399775B2