Ammonium Chloride → HCID 86587542, compound
Reaction equation
[CH3:1][N:2]([CH2:10][CH2:11][CH:12]=[O:13])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[CH2:14]([Mg]Cl)[CH2:15][CH2:16][CH3:17].[Cl-].[NH4+]>O1CCCC1>[OH:13][CH:12]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:11][CH2:10][N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:6])[CH3:7]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Methyl-(3-oxopropyl)carbamic acid, 1,1-dimethylethyl ester (2.00 g, 10.7 mmol) was dissolved in tetrahydrofuran (20 ml) under nitrogen and cooled to 0° C. with stirring. To the resulting solution was added n-butylmagnesium chloride and the mixture stirred at 0° C. for a further 30 minutes and then allowed to warm to room temperature with stirring over 20 h. The mixture was then poured into saturated ammonium chloride solution and then extracted with diethyl ether three times. The combined organic fractions were then washed with brine and dried over magnesium sulfate. The solvent was evaporated and the residue eluted down a flash chromatography column using 40% diethyl ether/isohexane as eluent to give 1.70 g (65%) of the title compound as an oil.
Workup
- stirringthe mixture stirred at 0° C. for a further 30 minutes
- temperatureto warm to room temperature
- stirringwith stirring over 20 h
- extractionextracted with diethyl ether three times
- washThe combined organic fractions were then washed with brine
- dry with materialdried over magnesium sulfate
- customThe solvent was evaporated
- washthe residue eluted down a flash chromatography column
Sources & evidence
- ORD record
- ord-4ceaf21c7df3403c91abc1cea555d38d
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06900243B2
Reaction notes
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