Ammonium Chloride → HCID 86649678、化合物

HRID 1804746ノート

反応式

HRID 1804746 の反応式
[Na].[N:2]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[N+:3]=[N-:4].[CH3:11][Si:12]([CH3:22])([CH3:21])[C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.[NH4+].[Cl-]>CCO>[N:2]([C:5](=[CH:16][C:15]1[CH:18]=[CH:19][CH:20]=[C:13]([Si:12]([CH3:11])([CH3:22])[CH3:21])[CH:14]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[N+:3]=[N-:4]

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 69480Acetic acid, azido-, ethyl esterHCID 5360545SodiumHCID 11823172HCID 11823172、化合物

生成物 1

HCID 86649678HCID 86649678、化合物収率 26.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
-10 °C

実験手順

To a solution of 2 g (87.5 mmol) of sodium in 30 mL of anhydrous EtOH, maintained under a nitrogen atmosphere and cooled to −10° C., is added, dropwise, a mixture of 31.4 mL (87.5 mmol) of ethyl azidoacetate (at 34% in CH2Cl2) and 3.9 g (21.87 mmol) of 3-trimethylsilylbenzaldehyde prepared according to the procedure described in the preceding step, diluted with 3 mL of EtOH. The reaction mixture is stirred at 0° C. for 4 hours. It is then hydrolysed by adding, with vigorous stirring, 100 mL of aqueous NH4Cl solution (30%). The aqueous phase is extracted with 3×50 mL of EtOAc. The combined organic phases are washed with water, dried over Na2SO4 and concentrated under reduced pressure. The crude reaction product is purified by chromatography on a column of silica gel, eluting with an isocratic mixture of heptane and CH2Cl2 (80/20). 1.7 g of the expected ethyl 2-azido-3-(3-trimethylsilylphenyl)propenoate are thus isolated in the form of a yellow oil.

後処理

  1. additionis added
  2. customprepared
  3. extractionThe aqueous phase is extracted with 3×50 mL of EtOAc
  4. washThe combined organic phases are washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude reaction product
  8. customis purified by chromatography on a column of silica gel
  9. washeluting with an isocratic mixture of heptane and CH2Cl2 (80/20)

出典と根拠

ORDレコード
ord-309d3ecaa63b44feb7f161081ff882e8
出典データセット
uspto-grants-2013_01
特許番号
US08354425B2

反応ノート

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