Dichloromethane → Benzyl [1-(4-nitrobenzyl)but-3-enyl]ethoxymethylcarbamate

HRID 1584757Notes

Reaction equation

[OH-].[Na+].C(Cl)Cl.[N+:6]([C:9]1[CH:30]=[CH:29][C:12]([CH2:13][CH:14]([NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:15][CH:16]=[CH2:17])=[CH:11][CH:10]=1)([O-:8])=[O:7].[CH2:31]([O:33][CH2:34]Cl)[CH3:32]>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.O>[N+:6]([C:9]1[CH:10]=[CH:11][C:12]([CH2:13][CH:14]([N:18]([CH2:34][O:33][CH2:31][CH3:32])[C:19](=[O:28])[O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:15][CH:16]=[CH2:17])=[CH:29][CH:30]=1)([O-:8])=[O:7]

Participants

Conditions

Temperature: 7.5 °C

Procedure

A mixture of 10 ml of 50% strength aqueous sodium hydroxide solution, 25 ml of methylene chloride and 130 mg (0.4 mmol) of benzyltributylammonium chloride is vigorously stirred at 5-10° C. Benzyl [1-(4-nitrobenzyl)but-3-enyl]carbamate (6.8 g, 20.0 mmol) is added in one portion followed by 2.64 g (28 mmol) of chloromethyl ethyl ether over a period of 2 hours. The mixture is then stirred at room temperature for 1 hour, diluted with ice and water and extracted with methylene chloride. The organic phase is dried over sodium sulfate, evaporated and chromatographed on silica gel (hexane/ethyl acetate (10:1)). The title compound is obtained as a colourless oil. TLC: ethyl acetate/hexane (1:3) Rf =0.41. FD-MS: M+ : 398.

Workup

stirringThe mixture is then stirred at room temperature for 1 hour
extractionextracted with methylene chloride
dry with materialThe organic phase is dried over sodium sulfate
customevaporated
customchromatographed on silica gel (hexane/ethyl acetate (10:1))

Sources & evidence

ORD record: ord-eb413f345e2749b0b366a3831118364c
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05935951

Reaction notes

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