Sodium Chloride → HCID 12794996, compound
Reaction equation
[CH2:1]([CH2:4][OH:5])[CH2:2][NH2:3].[CH3:6][O:7][C:8]([CH2:10][C:11]([CH2:13][C:14]([O:16][CH3:17])=[O:15])=O)=[O:9].Br[CH2:19][C:20](C)=O.[Cl-].[Na+]>O>[OH:5][CH2:4][CH2:1][CH2:2][N:3]1[CH:20]=[CH:19][C:10]([C:8]([O:7][CH3:6])=[O:9])=[C:11]1[CH2:13][C:14]([O:16][CH3:17])=[O:15]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
To a solution of propanolamine in water there is added dimethyl 1,3-acetonedicarboxylate. The resultant mixture is rapidly cooled to -10° C. and treated dropwise, over a 15 minute period, with stirring, with 1-bromoacetone, whilst maintaining the reaction mixture at a temperature not higher than 40° C. When the addition is completed the dark reaction mixture is stirred for an additional hour at room temperature, and then poured into a mixture of hydrochloric acid-ice, saturated with solid sodium chloride and extracted with ethyl acetate (3×100 ml.). The combined organic extract is washed with cold water to neutrality, dried with anhydrous sodium sulfate and evaporated to dryness under reduced pressure. Chromatography of the residue on silica gel, using hexane:ethyl acetate as eluant, affords methyl N-(3-hydroxypropyl)-3-carbomethoxy-4-methylpyrrole-2-acetate (IV, R=CH3, n=1).
Workup
- additiontreated dropwise, over a 15 minute period
- additionWhen the addition
- customthe dark reaction mixture
- extractionextracted with ethyl acetate (3×100 ml.)
- extractionThe combined organic extract
- washis washed with cold water to neutrality
- dry with materialdried with anhydrous sodium sulfate
- customevaporated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-7c2d57cfa3db46a7a3c6f6d69474e036
- Source dataset
- uspto-grants-1983_10
- Patent number
- US04410534
Reaction notes
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