Ammonium Chloride → HCID 86649678, compound

HRID 1948784Notes

Reaction equation

HRID 1948784 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 86649678HCID 86649678, compoundYield 26.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
-10 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-3afacf1df990473d8d563892e941e2ac
Source dataset
uspto-grants-2013_03
Patent number
US08399491B2

Reaction notes

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