Hydrochloric Acid → HCID 17942764, compound

HRID 855733Notes

Reaction equation

HRID 855733 reaction equation
[CH:1]1([CH2:6][CH2:7][C:8](Cl)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:11][C:12]1([CH3:20])[O:17][C:16](=[O:18])[CH2:15][C:14](=[O:19])[O:13]1.N1C=CC=CC=1.Cl>C(Cl)Cl>[CH:1]1([CH2:6][CH2:7][C:8]([CH:15]2[C:16](=[O:18])[O:17][C:12]([CH3:20])([CH3:11])[O:13][C:14]2=[O:19])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 660393-Cyclopentylpropionyl chloride

Product 1

HCID 17942764HCID 17942764, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-Cyclopentylpropionyl chloride (0.64 ml, 4.16 mmol) was added to a solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (500 mg, 3.47 mmol) in anhydrous methylene chloride (10 ml). After cooling to 0° C., pyridine (0.56 ml, 6.94 mmol) was added in portions. After stirring for 1 hour at 0° C. and 2 hours at ambient temperature the mixture was poured onto water (20 ml) containing concentrated hydrochloric acid (0.5 ml). The organic layer was separated, washed with water, brine, dried (MgSO4) and the volatiles were removed by evaporation to give 5-(3-cyclopentylpropionyl)-2,2-dimethyl-1,3-dioxane-4,6-dione (900 mg, 96%).

Workup

  1. additionwas poured onto water (20 ml)
  2. customThe organic layer was separated
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. customthe volatiles were removed by evaporation

Sources & evidence

ORD record
ord-d7f29798a9d540aa8d6c3762290f26d4
Source dataset
uspto-grants-2007_08
Patent number
US07262201B1

Reaction notes

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