Tetrahydrofuran → HCID 55299493, compound

Temperature

-78 °C

Cyclopentanecarboxylic acid (1.10 g, 10.0 mmol) was placed in a round-bottomed bottomed flask, filled with nitrogen, and 30 mL of THF (30 mL) was added. The solution was cooled to −78° C., and LDA (8.8 mL, 2.5 m in hexane) was added dropwise. After being stirred for 30 min., the solution was bubbled by nitrogen stream containing formaldehyde gas (formaldehyde gas was in situ generated by thermal degradation of anhydrouse paraformaldehyde at 160° C.). When the reaction solution turned light yellow, the reaction mixture was quenched with a saturated aqueous NH4Cl solution at −78° C., and the organic material was extracted with EtOAc. The organic extracts were dried over MgSO4, filtered, and concentrated in vacuo to give the title compound.

1. additionwas added
2. customthe solution was bubbled by nitrogen stream
3. additioncontaining formaldehyde gas (formaldehyde gas
4. customgenerated by thermal degradation of anhydrouse paraformaldehyde at 160° C.
5. customthe reaction mixture was quenched with a saturated aqueous NH4Cl solution at −78° C.
6. extractionthe organic material was extracted with EtOAc
7. dry with materialThe organic extracts were dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-7ab256fbbe01490cac8fdf3ac9f222e0

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07989634B2