Benzene → HCID 131728530, compound

Powdered sodium-borohydride (0.33 g, 8.6 mmol) was added in portions at 0° C., to a solution of chloroacetic acid (1.68 g, 17 mmol) in THF (6 mL), and benzene (90 mL). Reaction mixture was warmed to room temperature and stirred for 1 h, and compound of Example 29a (1.3 g, 2.9 mmol) was added. Reaction mixture was refluxed for 3 h. Reaction mixture was cooled and quenched using sodium bicarbonate solution, and extracted with ethylacetate. Organic layer was washed with water (100 mL) and brine (50 mL). The crude product obtained was purified by column chromatography (silica gel, ethylacetate/pet-ether) to obtain the title compound. Yield: 1.25 g (87%); 1H NMR (DMSO-d6, 300 MHz): δ 2.00 (t, 2H, CH2), 2.63 (s, 3H, CH3), 3.66 (t, 2H, CH2), 3.69-3.80 (m, 6H, 3×CH2), 3.85 (s, 3H, OCH3), 5.16 (s, 2H, CH2), 6.74 (s, 1H, Ar), 6.85 (s, 1H, Ar), 8.08 (s, 1H, Ar), 8.14 (s, 1H, Ar); MS: m/e (EI) 506 (M+).

1. customReaction mixture
2. customReaction mixture
3. temperaturewas refluxed for 3 h
4. customReaction mixture
5. temperaturewas cooled
6. customquenched
7. extractionextracted with ethylacetate
8. washOrganic layer was washed with water (100 mL) and brine (50 mL)
9. customThe crude product obtained
10. customwas purified by column chromatography (silica gel, ethylacetate/pet-ether)

ORD record

ord-ab0327e56d6b4912aef7554803e34e39

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07834052B2