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

HRID 1070038ノート

反応式

HRID 1070038 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 853082792-Hydroxyimino-2-(3-phenoxyphenyl)acetonitrile収率 45%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒2 回HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4315ba764d5148efaf6776f8b73e386d
出典データセット
uspto-grants-2001_06
特許番号
US06251926B1

反応ノート

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