Tetrahydrofuran → HCID 46181478, compound

Temperature

5 °C

A 1.0 M solution of potassium t-butoxide in t-butanol (0.3 mL) was added to a 8 mL vial fitted with a septa cap containing 0.3 mL of dry THF and 30 mg (0.3 mmoles) of 3-hydroxy cylcopentanol at 5° C. The mixture was stirred for 0.5 h at 5° C., after which time 0.3 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., and quenched with 2 mL of water, diluted with 2 mL of methyl tert-butyl ether. The vial was shaken vigourously and the phases allowed to separate. The aqueous layer was removed with a pipette, and the organic layer washed with another 2 mL of water. The organic phase was dried (MgSO4), concentrated in vacuo, and the residue purified by reverse phase HPLC (Shimadzu) to give 36 mg (52%) of the title compound. GC/MS: 235 (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. customquenched with 2 mL of water
8. additiondiluted with 2 mL of methyl tert-butyl ether
9. stirringThe vial was shaken vigourously
10. customto separate
11. customThe aqueous layer was removed with a pipette
12. washthe organic layer washed with another 2 mL of water
13. dry with materialThe organic phase was dried (MgSO4)
14. concentrationconcentrated in vacuo
15. customthe residue purified by reverse phase HPLC (Shimadzu)

ORD record

ord-0171bb6dfd914455bd397d0af991b7a6

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07670613B2