Isoamyl Nitrite → 2-Hydroxyimino-2-(3-phenoxyphenyl)acetonitrile

HRID 2299712노트

반응식

HRID 2299712 반응식
[O-]CC.[Na+].[Na].[O:6]([C:13]1[CH:14]=[C:15]([CH2:19][C:20]#[N:21])[CH:16]=[CH:17][CH:18]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N:22](OCCC(C)C)=[O:23]>C(O)C.C(OCC)C>[OH:23][N:22]=[C:19]([C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([O:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:14]=1)[C:20]#[N:21]

참가 물질

7

반응물 4

HCID 8053Isoamyl NitriteHCID 40075m-Phenoxybenzyl cyanideHCID 2723922Sodium ethoxideHCID 5360545Sodium

생성물 1

HCID 853082792-Hydroxyimino-2-(3-phenoxyphenyl)acetonitrile수율 45%

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 3283Diethyl Ether용매

실험 절차

To a solution of sodium ethoxide prepared from sodium (1.09 g) and ethanol (20 ml), a solution of 3-phenoxyphenylacetonitrile (8.30 g) in ethanol (15 ml) was added dropwise at 0° C., and then isoamyl nitrite (7.99 ml) was added dropwise. After stirring for 15 hours at room temperature, diethyl ether was added and the mixture was washed sequentially with 1N HCl, aqueous sodium bicarbonate and then saturated aqueous sodium chloride. The diethyl ether layer was dried (MgSO4), concentrated, and the residue was subjected to column chromatography on silica gel. The crystals obtained from a fraction eluted with ethyl acetate-hexane (1:4, v/v) were recrystallized with ethyl acetate-hexane to obtain 2-hydroxyimino-2-(3-phenoxyphenyl)acetonitrile (4.25 g, yield: 45%) as pale-yellow crystals. A mixture of the E- form and the Z- form. m.p. 124-125° C.

후처리

  1. washthe mixture was washed sequentially with 1N HCl, aqueous sodium bicarbonate
  2. dry with materialThe diethyl ether layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customThe crystals obtained from a fraction
  5. washeluted with ethyl acetate-hexane (1:4, v/v)
  6. customwere recrystallized with ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-20613cfbb7604198840da3b3eac470b1
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06495581B1

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