Chloroform → tert-Butyl 2,2-difluoro-3-[(2-methylacryloyl)oxy]pentanoate

HRID 2047954Notes

Reaction equation

HRID 2047954 reaction equation
[F:1][C:2]([F:14])([CH:10]([OH:13])[CH2:11][CH3:12])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].C(Cl)(Cl)Cl.[C:19](Cl)(=[O:23])[C:20]([CH3:22])=[CH2:21].C(N(CC)CC)C>O>[C:19]([O:13][CH:10]([CH2:11][CH3:12])[C:2]([C:3]([O:5][C:6]([CH3:7])([CH3:9])[CH3:8])=[O:4])([F:14])[F:1])(=[O:23])[C:20]([CH3:22])=[CH2:21]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 58239498HCID 58239498, compound

Product 1

HCID 59863855tert-Butyl 2,2-difluoro-3-[(2-methylacryloyl)oxy]pentanoateYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

A 25 mL reactor was charged with 1.50 g (5.6 mmol) of t-butyl 2,2-difluoro-3-hydroxypentanoate and 15 mL of chloroform, 10 mg of NONFLEX MBP, 1.17 g (11.2 mmol, 2 eq) of methacrylic chloride, and 0.87 g (8.6 mmol, 1.5 eq) of triethylamine, followed by stirring at 55° C. for 24 hr. Then, 15 mL of water was added, followed by extraction with chloroform one time. The obtained organic layer was washed with saturated sodium hydrogencarbonate and water, followed by removal of water with magnesium sulfate. After conducting filtration, chloroform was distilled off, thereby obtaining 1.57 g of the target 1-(t-butoxycarbonyl)-1,1-difluoro-2-butyl methacrylate. Upon this, purity was 58%, and yield was 58%.

Workup

  1. extractionfollowed by extraction with chloroform one time
  2. washThe obtained organic layer was washed with saturated sodium hydrogencarbonate and water
  3. customfollowed by removal of water with magnesium sulfate
  4. filtrationfiltration, chloroform
  5. distillationwas distilled off

Sources & evidence

ORD record
ord-f1a2d43f19624504b1216f8e7afa1ead
Source dataset
uspto-grants-2013_11
Patent number
US08592622B2

Reaction notes

Loading…