1,4-Dioxane → HCID 23361366, 화합물

HRID 233287노트

반응식

HRID 233287 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 23361366HCID 23361366, 화합물수율 99.5%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d9adc0af8aed40079fabb92dd0acb956
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05591862

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