Pyridine → HCID 68771741, compound

HRID 1942579Notes

Reaction equation

HRID 1942579 reaction equation
N1C=CC=CC=1.[CH3:7][C:8]1([CH3:16])[O:15][C:13](=[O:14])[CH2:12][C:10](=[O:11])[O:9]1.[C:17](Cl)(=[O:31])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]C>C(Cl)Cl>[OH:31][C:17](=[C:12]1[C:13](=[O:14])[O:15][C:8]([CH3:16])([CH3:7])[O:9][C:10]1=[O:11])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 1049PyridineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 66986Myristoyl chloride

Product 1

HCID 68771741HCID 68771741, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

14.3 mL of pyridine is added at 0° C., to a solution of Meldrum's acid (10.60 g, 73.5 mmol) in 70 mL of anhydrous CH2Cl2. After stirring for 15 min at this temperature, commercial tetradecanoyl chloride (18.16 g, 73.5 mmol) is added dropwise, so that the temperature remains below 10° C. After stirring for 2 h at 0° C. and for 1 h at ambient temperature, the reaction medium is washed with 50 mL of a 2N solution of HCl then 2×50 mL of water. After a last washing with a saturated aqueous solution of NaCl, the organic phase is dried over MgSO4, filtered and concentrated under vacuum. The oil obtained is crystallized by the addition of absolute ethanol then left overnight in the refrigerator. The solid is then filtered then rinsed with cold absolute ethanol before being dried in order to produce compound 17 (21.25 g, 59.9 mmol, 81%) in the form of a white solid.

Workup

  1. additionis added dropwise, so that the temperature
  2. customremains below 10° C
  3. washthe reaction medium is washed with 50 mL of a 2N solution of HCl
  4. washAfter a last washing with a saturated aqueous solution of NaCl
  5. dry with materialthe organic phase is dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe oil obtained
  9. customis crystallized by the addition of absolute ethanol
  10. waitthen left overnight in the refrigerator
  11. filtrationThe solid is then filtered
  12. washthen rinsed with cold absolute ethanol
  13. custombefore being dried in order

Sources & evidence

ORD record
ord-b022d44fd46c48af8e3e59367aa4d67a
Source dataset
uspto-grants-2013_03
Patent number
US08389569B2

Reaction notes

Loading…