Lithium Hexamethyldisilazide → HCID 86709726, compound

Temperature

0 °C

The solution of CH3P(Ph)3Br (268 mg, 0.736 mmol) in anhydrous THF (5 mL) was cooled to −78° C. under N2. LiHMDS (1 M in THF, 0.69 mL) was added dropwise via syringe. The mixture was stirred at 0° C. for 1 h then cooled down to −78° C. again. To it, was added the reactant carbaldehyde 155b (125 mg, 0.46 mmol) in anhydrous THF (5 mL) at −78° C. dropwise. The mixture was stirred at −78° C. to RT over 2 h period, then RT for 2 h. Reaction was monitored by TLC. After completion, the reaction was quenched by adding sat'd NH4Cl. It was extracted with EtOAc twice, washed with brine. The organic layer was dried through (Na2SO4), and concentrated; the residue was purified by CombiFlash on silica gel column using EtOAC/Hexane as eluents to give (3S,7aS)-3-(trichloromethyl)-7a-vinyltetrahydropyrrolo[1,2-c]oxazol-1(3H)-one 30 mg, 24%.

1. temperaturethen cooled down to −78° C. again
2. stirringThe mixture was stirred at −78° C. to RT over 2 h period
3. waitRT for 2 h
4. customReaction
5. customAfter completion, the reaction was quenched
6. additionby adding sat'd NH4Cl
7. extractionIt was extracted with EtOAc twice
8. washwashed with brine
9. dry with materialThe organic layer was dried through (Na2SO4)
10. concentrationconcentrated
11. customthe residue was purified by CombiFlash on silica gel column

ORD record

ord-f3a7ebd0219e47a5ad33ec402f3ddd07

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09145441B2