18-Crown-6 → HCID 59556579, compound

Temperature

-78 °C

A two-neck round bottom flask was charged with methyl 2-(bis(2,2,2-trifluoroethoxy)phosphoryl)acetate (0.235 ml, 1.109 mmol), 18-crown-6 (1465 mg, 5.54 mmol) and THF (15 ml). The mixture was then cooled to −78° C. under an atmosphere of nitrogen. Potassium bis(trimethylsilyl)amide (221 mg, 1.109 mmol) was added and the mixture stirred for a few minutes. 4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzaldehyde (380 mg, 1.109 mmol) was added and the mixture stirred at −78° C. for 90 minutes and then left to warm to room temperature overnight. Reaction was quenched by the addition of saturated NH 4Cl (aqueous). Mixture was separated and the aqueous layer was extracted with ether (3×10 mL). Combined organics were dried over MgSO4 and concentrated to give an off-white solid. Solid was triturated with MeOH and collected by vacuum filtration and washed with MeOH (3×10 mL). Collected solid was dried overnight in a vacuum oven to give (Z)-methyl 3-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)acrylate (325 mg, 73.5%).

1. stirringthe mixture stirred at −78° C. for 90 minutes
2. waitleft
3. temperatureto warm to room temperature overnight
4. customReaction
5. customwas quenched by the addition of saturated NH
6. customMixture was separated
7. extractionthe aqueous layer was extracted with ether (3×10 mL)
8. dry with materialCombined organics were dried over MgSO4
9. concentrationconcentrated
10. customto give an off-white solid
11. customSolid was triturated with MeOH
12. filtrationcollected by vacuum filtration
13. washwashed with MeOH (3×10 mL)
14. customCollected solid
15. customwas dried overnight in a vacuum oven

ORD record

ord-a66d6a1f2ade4ddfa5f3307731e90a5b

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07834039B2