Tetrahydrofuran → Methacrylic acid 1-(1-ethylcyclopentyloxycarbonyl)-1,1-difluoro-2-butyl ester
Reaction equation
[OH:1][C:2]([C:4]([F:15])([F:14])[CH:5]([O:8][C:9](=[O:13])[C:10]([CH3:12])=[CH2:11])[CH2:6][CH3:7])=[O:3].C1COCC1.C(N(CC)CC)C.Cl[C:29]1([CH2:34][CH3:35])[CH2:33][CH2:32][CH2:31][CH2:30]1>O>[CH2:34]([C:29]1([O:3][C:2]([C:4]([F:14])([F:15])[CH:5]([O:8][C:9](=[O:13])[C:10]([CH3:12])=[CH2:11])[CH2:6][CH3:7])=[O:1])[CH2:33][CH2:32][CH2:31][CH2:30]1)[CH3:35]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A 2 L reactor was charged under nitrogen with 5.6 g (purity 78%, 20.0 mmol) of methacrylic acid 1-hydroxycarbonyl-1,1-difluoro-2-butyl ester and 240 mL of THF (dehydrated), followed by cooling down to 0° C., adding 5.2 mL (37.6 mmol/1.9 equivalents) of triethylamine, and stirring at 0° C. for 10 minutes. Then, furthermore 14.24 g (3.2 mmol/1.6 equivalents) of 1-chloro-1-ethylcyclopentane was added, followed by stirring at 0° C. for 20 minutes. To the reaction liquid 800 mL of water was added, followed by extraction two times with diisopropyl ether, removing water by magnesium sulfate, conducting a filtration, and distilling diisopropyl ether out, thereby obtaining 5.52 g of the target methacrylic acid 1-(1-ethylcyclopentyloxycarbonyl)-1,1-difluoro-2-butyl ester. Upon this, purity was 96%, and yield was 83%.
Workup
- stirringby stirring at 0° C. for 20 minutes
- additionwas added
- extractionfollowed by extraction two times with diisopropyl ether
- customremoving water by magnesium sulfate
- filtrationa filtration
- distillationdistilling diisopropyl ether out
Sources & evidence
- ORD record
- ord-096255fd802f46a29de630ec9c9026b9
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08663903B2
Reaction notes
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