Hydrochloric Acid → HCID 22259314, compound

HRID 1610990Notes

Reaction equation

HRID 1610990 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]2[O:12][CH:13]=[C:14]([CH2:16][C:17](OCC)=[O:18])[N:15]=2)=[CH:5][CH:4]=1.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].Cl>C1COCC1.C(O)C>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]2[O:12][CH:13]=[C:14]([CH2:16][CH2:17][OH:18])[N:15]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 86595243HCID 86595243, compound

Product 1

HCID 22259314HCID 22259314, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

Ethyl [[(E)-2-(4-(trifluoromethyl)phenyl)ethenyl]-1,3-oxazol-4-yl]acetate (1.72 g) was added to a suspension of calcium chloride (2.35 g) and sodium borohydride (1.60 g) in THF-ethanol (10 ml- 10 ml) at 0° C., and the mixture was stirred for 1 hr. The reaction mixture was combined with 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate:hexane=1:1 to ethyl acetate) to give the titled compound (1.27 g) as a colorless crystal powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate:hexane=1:1 to ethyl acetate)

Sources & evidence

ORD record
ord-d9a075a772e44804849e37bc3a5e255e
Source dataset
uspto-grants-2006_01
Patent number
US06984653B2

Reaction notes

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