1,4-Dioxane → HCID 23361366, compound

HRID 233287Notes

Reaction equation

HRID 233287 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]([CH3:31])=[C:11]([CH2:13][CH2:14][O:15][C:16]2[CH:30]=[CH:29][C:19]([CH:20]=[C:21]([C:27]#[N:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18][CH:17]=2)[N:12]=1.O1CCOCC1.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]([CH3:31])=[C:11]([CH2:13][CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:20][CH:21]([C:27]#[N:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:29][CH:30]=2)[N:12]=1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 4311764Sodium borohydrideHCID 54471283HCID 54471283, compound

Product 1

HCID 23361366HCID 23361366, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of ethyl 4-[2-[2-(2-chlorophenyl)-5-methyl-4-oxazolyl]ethoxy]-α-cyanocinnamate (2.25 g) and dioxane (30 ml)--ethanol (30 ml) was added sodium borohydride (0.06 g) under ice-cooling. The mixture was stirred for one hour at the same temperature. The reaction mixture was poured into ice-water, which was made acid and subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), then the solvent was distilled off under reduced pressure. The residue was subjected to a silica gel column chromatography. From the fractions eluted with chloroform-methanol (50:1, v/v), was obtained ethyl 3-[4-[2-[2-(2-chlorophenyl)-5-methyl-4-oxazolyl]ethoxy]phenyl]-2-cyanopropionate (2.25 g, quant.) as an oily product. NMR(δ ppm in CDCl3): 1.27(3H,t,J=7Hz), 2.39(3H,s), 3.00(2H,t,J=6.5Hz), 3.12(1H,dd,J=14&8Hz), 3.22(1H,dd,J=14&6Hz), 3.66(1H,dd,J=8&6Hz), 4.22(2H,q,J=7Hz), 4.24(2H,t,J=6.5Hz), 6.87(2H,d,J=9Hz), 7.17(2H,d,J=9Hz), 7.25-7.5(3H,m), 7.85-8.0(1H,m).

Workup

  1. temperaturecooling
  2. extractionsubjected to extraction with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationthe solvent was distilled off under reduced pressure
  6. washFrom the fractions eluted with chloroform-methanol (50:1

Sources & evidence

ORD record
ord-d9adc0af8aed40079fabb92dd0acb956
Source dataset
uspto-grants-1997_01
Patent number
US05591862

Reaction notes

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