Ethyl bromoacetate → Ethyl [2-ethyl-4-(hydroxymethyl)phenoxy]acetate
Reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH2:9][OH:10])[CH:6]=[CH:5][C:4]=1[OH:11])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].CCOC(C)=O>C(#N)C.O>[CH2:1]([C:3]1[CH:8]=[C:7]([CH2:9][OH:10])[CH:6]=[CH:5][C:4]=1[O:11][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:2]Participants
Procedure
To a solution of 2-ethyl-4-(hydroxymethyl)phenol (3.67 g, 24.1 mmol) in anhydrous acetonitrile (125 mL) was added caesium carbonate (8.65 g, 26.6 mmol), the reaction mixture was then flushed with nitrogen and cooled to 0° C. before addition of ethyl bromoacetate (2.68 mL, 24.1 mmol). The reaction mixture was allowed to gradually attain room temperature and stirred for 18 h. Further ethylbromoacetate (0.26 mL, 2.4 mmol) was added and stirring continued for 4 h. The reaction mixture was diluted with water (100 mL) and then extracted EtOAc (2×100 mL). The combined organic extracts were dried (MgSO4) filtered and evaporated. Purification by Biotage™ chromatography (Silica, 90 g) eluting 4:1 cyclohexane:EtOAc, then EtOAc afforded the title compound as a pale yellow gum (3.54 g).
Workup
- customthe reaction mixture was then flushed with nitrogen
- customwas allowed to gradually attain room temperature
- stirringstirring
- waitcontinued for 4 h
- dry with materialThe combined organic extracts were dried (MgSO4)
- filtrationfiltered
- customevaporated
- customPurification by Biotage™ chromatography (Silica, 90 g)
- washeluting 4:1 cyclohexane
Sources & evidence
- ORD record
- ord-4d3f48b3107a49d9a400a6667ca2203e
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07199239B2
Reaction notes
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