Chloromethyl Methyl Ether → 1-(Methoxymethyl)oxycarbonyl-1,1-difluoro-2-butyl methacrylate

HRID 2047953Notes

Reaction equation

[C:1]([O:6][CH:7]([CH2:14][CH3:15])[C:8]([C:11]([OH:13])=[O:12])([F:10])[F:9])(=[O:5])[C:2]([CH3:4])=[CH2:3].C1[CH2:20][O:19][CH2:18]C1.COCCl>O>[C:1]([O:6][CH:7]([CH2:14][CH3:15])[C:8]([C:11]([O:13][CH2:18][O:19][CH3:20])=[O:12])([F:10])[F:9])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

Conditions

Temperature: 0 °C

Procedure

Under nitrogen, a 20 mL reactor was charged with 70 mg (0.25 mmol) of 1-hydroxycarbonyl-1,1-difluoro-2-butyl methacrylate (purity: 78%) and 3 mL of THF (dehydrated one), followed by cooling to 0° C. Then, 65 μL (0.47 mmol, 1.9 eq) was added, followed by stirring at 0° C. for 10 min. Then, 30 μL (0.40 mmol, 1.6 eq) of chloromethyl methyl ether was added, followed by stirring at 0° C. for 20 min. Then, 5 mL of water was added to the reaction solution, followed by extraction with diisopropyl ether two times and removal of water with magnesium sulfate. After conducting filtration, diisopropyl ether was distilled off, thereby obtaining 58 mg of the target 1-(methoxymethyl)oxycarbonyl-1,1-difluoro-2-butyl methacrylate. Upon this, purity was 96%, and yield was 83%.

Workup

additionThen, 65 μL (0.47 mmol, 1.9 eq) was added
stirringby stirring at 0° C. for 20 min
extractionfollowed by extraction with diisopropyl ether two times and removal of water with magnesium sulfate
filtrationfiltration, diisopropyl ether
distillationwas distilled off

Sources & evidence

ORD record: ord-b0b8664efa1940e492a87844a9c86306
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592622B2

Reaction notes

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