Water → HCID 68546191, compound

Temperature

5 °C

A 1.0 M solution of potassium t-butoxide in t-butanol (3.2 mL) was added to a 16 mL vial fitted with a septa cap containing 3 mL of dry THF and 300 mg (3 mmoles) of cis-1,2-dihydroxy cylcopentanol at 5° C. The mixture was stirred for 0.5 h at 5° C., after which time 3 mL of a 1.0 M THF solution of 4-fluoro-2-chloro-benzonitrile was added. The reaction was stirred at 5° C. for 3 h and then allowed to warm to room temperature and stirred overnight at room temperature. The reaction mixture was cooled to 0° C., poured into a seperatory funnel containing 15 mL of water, and extracted with 20 mL of methyl tert-butyl ether. The organic phase was washed with water, brine, dried (MgSO4), concentrated in vacuo, and the residue purified by reverse phase HPLC (Shimadzu) to give 185 mg 2-Chloro-4-(cis-2-hydroxy-cyclopentyloxy)-benzonitrile. GC/MS: 237 (M/Z for C13H14ClNO).

1. customvial fitted with a septa
2. customcap
3. stirringThe reaction was stirred at 5° C. for 3 h
4. temperatureto warm to room temperature
5. stirringstirred overnight at room temperature
6. temperatureThe reaction mixture was cooled to 0° C.
7. additionpoured into a seperatory funnel
8. extractionextracted with 20 mL of methyl tert-butyl ether
9. washThe organic phase was washed with water, brine
10. dry with materialdried (MgSO4)
11. concentrationconcentrated in vacuo
12. customthe residue purified by reverse phase HPLC (Shimadzu)

ORD record

ord-50e515f642594d17866906c48abed5ef

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07670613B2