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

HRID 1363909Notes

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-edd60f31e4f040608c955d04a4b62784
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07887990B2

Reaction notes

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