Hydrochloric Acid → HCID 19973084, compound

HRID 2380305Notes

Reaction equation

HRID 2380305 reaction equation
Cl[CH2:2][C:3]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[F:20])([OH:12])[C:4]([F:11])([F:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6].N12CCCN=C1CCCCC2.O.Cl>C(Cl)Cl>[F:20][C:14]1[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:13]=1[C:3]1([O:12][CH2:2]1)[C:4]([F:11])([F:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 19973114HCID 19973114, compound

Product 1

HCID 19973084HCID 19973084, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 150 ml of methylene chloride was dissolved 15.7 g of ethyl 4-chloro-3-(2,4-difluorophenyl)-2,2-difluoro-3-hydroxybutyrate. To the solution was dropwise added 8.4 g of 1,8-diazabicyclo[5.4.0]undec-7-ene at 5°-10° C. The mixture was subjected to reaction at the same temperature for 2 hours. The resulting reaction mixture was introduced into 150 ml of water and adjusted to pH 1.0 with 6N hydrochloric acid. The organic layer was separated, washed with a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by a column chromatography (eluant: n-hexane/toluene=2/1) to obtain 11.1 g of oily ethyl 3-(2,4-difluorophenyl)-3,4-epoxy-2,2-difluorobutyrate.

Workup

  1. customat 5°-10° C
  2. customThe mixture was subjected to reaction at the same temperature for 2 hours
  3. customThe resulting reaction mixture
  4. customThe organic layer was separated
  5. washwashed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by a column chromatography (eluant: n-hexane/toluene=2/1)

Sources & evidence

ORD record
ord-f6b5c2eb557f451ebc83e38dd0822ec2
Source dataset
uspto-grants-1994_11
Patent number
US05366989

Reaction notes

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