Ethanol → HCID 178473075, compound
Reaction equation
[H-].[Na+].[N+:3]([C:6]1[NH:7][CH:8]=[C:9]([CH2:11][C:12]([F:16])([F:15])[CH2:13][OH:14])[N:10]=1)([O-:5])=[O:4].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C(O)C>C1COCC1>[N+:3]([C:6]1[NH:7][CH:8]=[C:9]([CH2:11][C:12]([F:16])([F:15])[CH2:13][O:14][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:10]=1)([O-:5])=[O:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -50 °C
Procedure
To a suspension of sodium hydride (500 mg, 20.8 mmol) in dry THF (20 ml) which was cooled at -50° C., a solution of 3-(2'-nitroimidazolyl)-2,2-difluoropropanol (2.0 g, 9.6 mmol) in dry THF (10 ml) and then a solution of ethyl bromoacetate (2.4 g, 14.4 mmol) in dry THF were dropwise added. Then, the reaction mixture was gradually warmed to a room temperature and stirred for 4 hours at the temperature. After the reaction, the mixture was cooled by ice. Ethanol (2 ml) was added to the mixture, concentrated and partitioned between ethyl acetate and water. The organic phase was dried over magnesium sulfate, filtered, concentrated and purified by silica gel column chromatography to obtain ethyl 2-[3'-(2"-nitroimidazolyl)-2',2'-difluoropropoxy]acetate (2.4 g)
Workup
- temperatureThen, the reaction mixture was gradually warmed to a room temperature
- customAfter the reaction
- temperaturethe mixture was cooled by ice
- concentrationconcentrated
- custompartitioned between ethyl acetate and water
- dry with materialThe organic phase was dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- custompurified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-f3720f7ffb9546678e6c66831a165a8f
- Source dataset
- uspto-grants-1990_12
- Patent number
- US04977273
Reaction notes
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