Pyridine → 5-Cyclopentanecarbonyl-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 1799421Notes

Reaction equation

[CH:1]1([C:6](Cl)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:9]1(=[O:18])[O:17][C:14]([CH3:16])([CH3:15])[O:13][C:11](=[O:12])[CH2:10]1.N1C=CC=CC=1>C(Cl)Cl>[CH:1]1([C:6]([CH:10]2[C:9](=[O:18])[O:17][C:14]([CH3:16])([CH3:15])[O:13][C:11]2=[O:12])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 5 °C

Procedure

A solution of cyclopentanecarbonyl chloride (1.100 mL, 9.05 mmol) in DCM (5 mL) was added dropwise to a stirred solution of isopropylidene malonate (1.304 g, 9.05 mmol), and pyridine (1.464 mL, 18.10 mmol) in DCM (20 mL) at 5° C., over a period of 10 minutes under nitrogen. The resulting solution was stirred at 5° C. for 1 hour and then allowed to warm to 20° C. and stirred for another hour. The reaction mixture was diluted with DCM (100 mL), and washed sequentially with 2M HCl (2×50 mL), water (50 mL), and saturated brine (50 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product, 5-(cyclopentanecarbonyl)-2,2-dimethyl-1,3-dioxane-4,6-dione (2.100 g, 97%) as a brown oil.

Workup

temperatureto warm to 20° C.
stirringstirred for another hour
washwashed sequentially with 2M HCl (2×50 mL), water (50 mL), and saturated brine (50 mL)
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-da77b65394f5430cbaca9aa574891385
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08344016B2

Reaction notes

Loading…