Hydrochloric Acid → HCID 51356771, compound

HRID 468564Notes

Reaction equation

HRID 468564 reaction equation
[CH:1]([Mg]Br)=[CH2:2].[F:5][C:6]1[CH:15]=[C:14]([F:16])[C:13]([F:17])=[CH:12][C:7]=1[CH2:8][C@H:9]1[CH2:11][O:10]1.Cl>C1COCC1>[F:5][C:6]1[CH:15]=[C:14]([F:16])[C:13]([F:17])=[CH:12][C:7]=1[CH2:8][C@H:9]([OH:10])[CH2:11][CH:1]=[CH2:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 53375443HCID 53375443, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 51356771HCID 51356771, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

CuBr(CH3)2 (3.3 g) was added to a reactor under the nitrogen atmosphere and cooled to −78° C. Vinylmagnesium bromide (240 ml) was added slowly to the reactor and stirred for 20 min. (2S)-2-(2,4,5-trifluorobenzyl)-oxirane (30 g) dissolved in THF (90 ml) was added dropwise slowly over 30 min, stirred at −78° C. for 30 min, and heated to 0° C. 2N aqueous HCl (300 ml) was added slowly to the resulting mixture, and the organic layer formed thereafter was separated. The separated organic layer was washed twice with satuated saline, dried over MgSO4, and filtered. The organic solvent was removed from the filtrate under a reduced pressure to obtain the title compound (34.5 g; yield: 100%).

Workup

  1. additionwas added dropwise slowly over 30 min
  2. temperatureheated to 0° C
  3. customthe organic layer formed
  4. customthereafter was separated
  5. washThe separated organic layer was washed twice with satuated saline
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customThe organic solvent was removed from the filtrate under a reduced pressure

Sources & evidence

ORD record
ord-f941c75cd1cd4c1fb318dff21f6d0f1e
Source dataset
uspto-grants-2014_01
Patent number
US08624026B2

Reaction notes

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