Benzoyl chloride → HCID 10903905, compound

HRID 1742084Notes

Reaction equation

[CH2:1]([O:3][CH:4]([O:6][C@H:7]1[C@@H:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:9][C:8]1=[O:17])[CH3:5])[CH3:2].C([Li])CCC.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1.CCCCCC.C(=O)(O)[O-].[Na+]>[C:23]([N:9]1[C@H:10]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@H:7]([O:6][CH:4]([O:3][CH2:1][CH3:2])[CH3:5])[C:8]1=[O:17])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 2.35 g (10 mmol) of cis-3-(1-ethoxyethoxy)-4-phenylazetidin-2-one in 40 mL of THF at -78° C. was added 6.1 mL (10.07 mmol) of a 1.65M solution of n-butyllithium in hexane. The mixture was stirred for 10 rain at -78° C. and a solution of 1.42 g (10.1 mmol) of benzoyl chloride in 10 mL of THF was added. The mixture was stirred at -78° C. for 1 h and diluted with 70 mL of saturated aqueous sodium bicarbonate and extracted with three 50 mL portions of ethyl acetate. The combined ethyl acetate extracts were dried over sodium sulfate and concentrated to give 3.45 g of an oil. Chromatography of the oil on silica gel eluted with ethyl acetate/hexane gave 3.22 g (95%) of cis-1-benzoyl-3-(1-ethoxyethoxy)-4-phenylazetidin-2-one (2) as a colorless oil.

Workup

stirringThe mixture was stirred at -78° C. for 1 h
extractionextracted with three 50 mL portions of ethyl acetate
dry with materialThe combined ethyl acetate extracts were dried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-0b43c31272ad41d3b77ff9c032981610
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05336785

Reaction notes

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