Hydrochloric Acid → HCID 57255911, compound

Dimethylsulphoxide (0,692 ml, 9.74 mmol) was injected dropwise into a stirred solution of oxalyl chloride (0,425 ml, 4.87 mmol) in dichloromethane (10 ml) at -78° under argon. After 2 min, a solution of ±5-(carbomethoxymethyl)-3-(5 -hydroxypentyl)-5-methoxycarbonyl-4,5-dihydroisoxazole (1.00 g, 3.48 mmol) in dichloromethane (5 ml) was added by cannula, and the mixture stirred for 30 min. Triethylamine (2.13 ml, 15.3 mmol) was injected, then the mixture allowed to warm to room temperature, poured into aqueous HCl, and extracted with dichloromethane. The extracts were washed with water, saturated aqueous NaCl, and dried (MgSO4). The solvent was removed under reduced pressure, and the crude aldehyde dried by evaporation of a toluene solution. Sodium hydride (60% oil suspension, 146 mg, 3.65 mmol) was washed with petroleum ether 40°-60° under argon, then heated with dimethylsulphoxide (5 ml) at 70-90° until all solid had dissolved. After cooling in a water bath, a solution of 2,4-bis(trifluoromethyl)benzyltriphenylphosphonium bromide (1.98 g, 3.48 mmol) in dimethylsulphoxide (15 ml) was added by cannula, and the mixture stirred at room temperature for 15 min. A solution of the crude aldehyde in dimethylsulphoxide (5 ml) was added, the mixture stirred for 20 h, then poured into aqueous HCl and extracted with ether. The extracts were washed with water, saturated aqueous NaCl, and dried (MgSO4). The solvent was removed under reduced pressure, and the residue purified by chromatography on silica gel (50-70% ether/petroleum ether 40°-60° ) to give the title compound (0.56 g, 33%) as a mixture of E and Z isomers.

1. extractionextracted with dichloromethane
2. washThe extracts were washed with water, saturated aqueous NaCl
3. dry with materialdried (MgSO4)
4. customThe solvent was removed under reduced pressure
5. dry with materialthe crude aldehyde dried by evaporation of a toluene solution
6. dissolutionhad dissolved
7. temperatureAfter cooling in a water bath
8. stirringthe mixture stirred at room temperature for 15 min
9. stirringthe mixture stirred for 20 h
10. extractionextracted with ether
11. washThe extracts were washed with water, saturated aqueous NaCl
12. dry with materialdried (MgSO4)
13. customThe solvent was removed under reduced pressure
14. customthe residue purified by chromatography on silica gel (50-70% ether/petroleum ether 40°-60° )

ORD record

ord-c0490036ae6e41b6989c4c0fab16358f

Source dataset

uspto-grants-1995_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05447954