Pyridine → 5-(1-Hydroxypropylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 1471326Notes

Reaction equation

HRID 1471326 reaction equation
[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[O:3]1.N1C=CC=CC=1.[C:17](Cl)(=[O:20])[CH2:18][CH3:19]>ClCCl.Cl>[OH:20][C:17](=[C:5]1[C:6](=[O:8])[O:7][C:2]([CH3:10])([CH3:1])[O:3][C:4]1=[O:9])[CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 1049PyridineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 62324Propionyl chloride

Product 1

HCID 547061775-(1-Hydroxypropylidene)-2,2-dimethyl-1,3-dioxane-4,6-dioneYield 93%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (4.41 g, 30.0 mmol) and pyridine (4.85 mL, 60.0 mmol) in dichloromethane (24 mL) at 0° C. under argon is added propionyl chloride (2.95 mL, 33.0 mmol). The mixture is stirred at 0° C. for 1 h and at room temperature for 1 h before being diluted with 2 N HCl (40 mL) and extracted with dichloromethane (80 mL). The extract is washed (brine) and dried. Solvent is removed at reduced pressure to give 5.57 g (93%) of 2 as a yellow solid, mp 43-46° C. IR 3345, 2856, 1715, 1456 cm−1; 1H NMR (CDCl3) δ 1.29 (t, J=7.5 Hz, 3H, CH2CH3), 1.76 (s, 6H, CH3, CH3), 3.14 (q, J=7.5 Hz, 2H, CH2CH3), 15.42 (bs, 1H, OH).

Workup

  1. extractionextracted with dichloromethane (80 mL)
  2. washThe extract is washed (brine)
  3. customdried
  4. customSolvent is removed at reduced pressure

Sources & evidence

ORD record
ord-e4661128dc8f497eb826148179dea5dc
Source dataset
uspto-grants-2015_04
Patent number
US09012217B2

Reaction notes

Loading…