2,2-Dimethyl-1,3-dioxane-4,6-dione → HCID 66767137, compound

HRID 1676313Notes

Reaction equation

HRID 1676313 reaction equation
CC1(C)[O:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])O1.[F:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18]/[N:19]=[C:20](\[CH3:23])/[CH:21]=O)=[CH:14][CH:13]=1>C1(C)C=CC=CC=1.C(O)(=O)C.N1CCCCC1>[F:11][C:12]1[CH:13]=[CH:14][C:15]([N:18]2[C:4](=[O:9])[C:5]([C:6]([OH:7])=[O:8])=[CH:21][C:20]([CH3:23])=[N:19]2)=[CH:16][CH:17]=1

Participants

6

Reactant 2

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 87365555HCID 87365555, compound

Product 1

HCID 66767137HCID 66767137, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalystHCID 1140TolueneSolvent

Procedure

A suspension of 2,2-dimethyl-1,3-dioxane-4,6-dione (0.71 g, 4.93 mmol) and (E)-2-(2-(4-fluorophenyl)hydrazono)propanal (0.889 g, 4.934 mmol) in toluene (20 mL) was treated with acetic acid (5 drops) and with piperidine (5 drops). The reaction mixture was then stirred at room temp for 17 hours. The precipitated condensation/cyclization product was filtered off and thoroughly washed with light petroleum to afford 0.709 g (58%) of the desired product. LRMS (ESI pos) m/e 249.1 (M+1). 1H-NMR (400 MHz, CD3OD) δ 7.96 (s, 1H), 7.61 (m, 2H), 7.24 (t, 2H), 2.45 (s, 3H); 19F NMR (376 MHz, CD3OD) δ −115.1.

Workup

  1. customThe precipitated condensation/cyclization product
  2. filtrationwas filtered off
  3. washthoroughly washed with light petroleum

Sources & evidence

ORD record
ord-6df56a581191468689a08b7f43aa3d5a
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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