HCID 11529906, compound → HCID 21932258, compound

Typical Procedures for the Preparation of Difluoromethyl Alkanes (11) from Alkyl-substitued Difluoromethyl Sulfones (4): Under an argon atmosphere, into a Schlenk flask containing 1,1-difluoro-5-phenylpentyl phenyl sulfone (4h) (100 mg, 0.31 mmol), anhydrous Na2HPO4 (308 mg, 2.2 mmol) in methanol (4 mL) at −20° C., was added 5% Na/Hg amalgam beads (700 mg, ca. 1.5 mmol Na). The reaction mixture was stirred at −20° C.˜0° C. for 1 h, and the completion of the reaction was monitored by 19F NMR. The methanol solution was decanted out, and the residue solids were washed with Et2O (5 mL×3). The volatile solvents of the combined solution were removed under vacuum, and the crude product was purified by a flash chromatography to give 1,1-difluoro-5-phenylpentane (11a) (50 mg, 87% yield) as a colorless liquid. 1H NMR (500 MHz, CDCl3): δ 1.51 (m, 2H); 1.70 (m, 2H); 1.86 (m, 2H); 2.64 (t, J=7.7 Hz, 2H); 5.80 (tt, J=57 Hz, 4.7 Hz, 1H); 7.19 (m, 3H); 7.30 (t, J=7.6 Hz, 2H). 13C NMR (125 MHz, CDCl3): δ 21.7 (t, J=5.4 Hz); 30.8; 33.9 (t, J=21 Hz); 117.3 (t, J=239 Hz); 125.8; 128.3; 141.9. 19F NMR (470 MHz, CDCl3): δ −116.2 (dt, J=57 Hz, 18 Hz, 1F).

1. customThe methanol solution was decanted out
2. washthe residue solids were washed with Et2O (5 mL×3)
3. customThe volatile solvents of the combined solution were removed under vacuum
4. customthe crude product was purified by a flash chromatography

ORD record

ord-2d1d3325db4346208c32e0479b5ad6f1

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07119232B2