Hydrochloric Acid → HCID 86685815, compound

HRID 1776003Notes

Reaction equation

HRID 1776003 reaction equation
[F:1][C:2]([F:14])([F:13])[CH:3]([O:7][C:8](=[O:12])[C:9]([CH3:11])=[CH2:10])[C:4]([OH:6])=[O:5].C1CCC(N=C=NC2CCCCC2)CC1.[F:30][C:31]([F:35])([F:34])[CH2:32]O.Cl>CN(C1C=CN=CC=1)C.ClCCl.C(OCC)(=O)C>[C:8]([O:7][CH:3]([C:4](=[O:6])[O:5][CH2:32][C:31]([F:35])([F:34])[F:30])[C:2]([F:13])([F:14])[F:1])(=[O:12])[C:9]([CH3:11])=[CH2:10]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 64092,2,2-TrifluoroethanolHCID 10868DicyclohexylcarbodiimideHCID 86685814HCID 86685814, compound

Product 1

HCID 86685815HCID 86685815, compoundYield 60.1%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, 3.18 g (15 mmol) of 3,3,3-trifluoro-2-(methacryloyloxy)propionic acid was added to 60 mL of a solution of 6.8 g (16.5 mmol) of DCC and 0.37 g (0.003 mol) of DMAP in dichloromethane, and 1.78 g (18 mmol) of 2,2,2-trifluoroethanol was added thereto at 0° C. The temperature of the mixture was equilibrated to the room temperature, and the mixture was stirred for 3 hrs. After disappearance of the raw material was confirmed by TLC, the reaction liquid was cooled to 0° C., and the reaction was stopped by adding 1 N hydrochloric acid. Thereafter, ethyl acetate was added to the reaction liquid and extraction was carried out three times, and the organic layer thus obtained was washed with water twice. Thereafter, purification by column chromatography gave 2.65 g of intended 1,1,1-trifluoro-3-oxo-3-(2,2,2-trifluoroethoxy)propan-2-yl methacrylate (M-6) (yield: 60%).

Workup

  1. additionwas added
  2. customat 0° C
  3. customwas equilibrated to the room temperature
  4. customthe reaction liquid
  5. customthe organic layer thus obtained
  6. washwas washed with water twice
  7. customThereafter, purification by column chromatography

Sources & evidence

ORD record
ord-8212f717b34a4ad985d4b7ccf0c01034
Source dataset
uspto-grants-2016_02
Patent number
US09261780B2

Reaction notes

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