Ammonium Chloride → HCID 86649678, compound

HRID 1911248Notes

Reaction equation

HRID 1911248 reaction equation
[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]

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

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.

Workup

  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)

Sources & evidence

ORD record
ord-9e52278c047a46758aab4e8a6f4a9984
Source dataset
uspto-grants-2013_12
Patent number
US08604050B2

Reaction notes

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