Ammonium Chloride → HCID 15476078, compound

Temperature

-50 °C

In a 500 ml flask as charged a 0.1 ML-1 dried THF solution containing 18 ml of lithium copper tetrachloride under a nitrogen atmosphere, followed by cooling to -50° C. The above prepared Grignard reagent was added thereto over 5 minutes, and the mixture was reacted at that temperature for 20 minutes. To the reaction mixture was added dropwise a solution of 8.07 g of (R)-glycidyl p-toluenesulfonate (produced by Aldrich Chemical Co., Inc.) in 70 ml of dried THF at the same temperature over 20 minutes through a dropping funnel, followed by further reacting for 1.5 hours. .The resulting reaction mixture was poured into a saturated ammonium chloride aqueous solution and extracted with diethyl ether. The extract was washed twice with a saturated sodium chloride aqueous solution, and the solvent was removed by distillation under reduced pressure to obtain 10.1 g (yield=95%) of a crude product. [α]D24 : -3.89° MS: 300 (M+) NMR (δ, ppm): 0.85 (6H, m), 1.3 (7H, m), 2.05 (1H, s), 2.43 (3H, s), 3.8 (1H, m), 3.97 (2H, m), 7.35 (2H, m), 7.8 (2H, m)

1. additionwas added
2. customthe mixture was reacted at that temperature for 20 minutes
3. waitby further reacting for 1.5 hours
4. custom.The resulting
5. customreaction mixture
6. extractionextracted with diethyl ether
7. washThe extract was washed twice with a saturated sodium chloride aqueous solution
8. customthe solvent was removed by distillation under reduced pressure

ORD record

ord-2f0a6187b6a948dfaecd547add0b5e2a

Source dataset

uspto-grants-1995_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05454976