Ammonium Chloride → HCID 86649678, 화합물

HRID 1948784노트

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HRID 1948784 반응식
[N:1]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+:2]=[N-:3].[CH3:10][Si:11]([CH3:21])([CH3:20])[C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=O.[Na].[NH4+].[Cl-]>CCO>[N:1]([C:4](=[CH:15][C:14]1[CH:17]=[CH:18][CH:19]=[C:12]([Si:11]([CH3:10])([CH3:21])[CH3:20])[CH:13]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+:2]=[N-:3]

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 69480Acetic acid, azido-, ethyl esterHCID 5360545SodiumHCID 11823172HCID 11823172, 화합물

생성물 1

HCID 86649678HCID 86649678, 화합물수율 26.9%

시약·촉매·용매 1

HCID 702Ethanol용매2회

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온도
-10 °C

실험 절차

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 stage 3.2, diluted in 3 ml of EtOH, is added dropwise 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. The reaction mixture is stirred at 0° C. for 4 h. It is subsequently hydrolysed by adding, with vigorous stirring, 100 ml of an aqueous solution of NH4Cl (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 reaction crude is purified by silica gel column chromatography, elution being carried out 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.

후처리

  1. customprepared
  2. temperaturemaintained under a nitrogen atmosphere
  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 reaction crude
  8. customis purified by silica gel column chromatography, elution
  9. additionbeing carried out with an isocratic mixture of heptane and CH2Cl2 (80/20)

출처 및 근거

ORD 기록
ord-3afacf1df990473d8d563892e941e2ac
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399491B2

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