Sodium Iodide → p-Nitrobenzyl 2-diazo-3-trimethylsilyloxy-3-butenoate

HRID 1460723Notes

Reaction equation

HRID 1460723 reaction equation
[N+:1](=[C:3]([C:17]([CH3:19])=[O:18])[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)=[O:5])=[N-:2].C(N(CC)CC)C.[CH3:27][Si:28](Cl)([CH3:30])[CH3:29].[I-].[Na+]>C(#N)C>[N+:1](=[C:3]([C:17]([O:18][Si:28]([CH3:30])([CH3:29])[CH3:27])=[CH2:19])[C:4]([O:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=1)=[O:5])=[N-:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 53872938HCID 53872938, compound

Product 1

HCID 54029376p-Nitrobenzyl 2-diazo-3-trimethylsilyloxy-3-butenoateYield 90.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To 1.5 ml of dry acetonitrile were added 100 mg (0.380 millimole) of p-nitrobenzyl 2-diazoacetoacetate, 64.8 μl (0.465 millimole) of triethylamine and 59 μl (0.465 millimole) of trimethylsilyl chloride. A solution obtained by dissolving 70 mg (0.467 millimole) of sodium iodide in 0.5 ml of dry acetonitrile was added dropwise thereto at a room temperature. After agitation for an hour, the reaction mixture was concentrated under a reduced pressure. After addition of 5 ml of hexane, insoluble materials were filtered off and the hexane was distilled off under a reduced pressure to give 115 mg (yield 90.1 %) of the desired compound in a yellow solid.

Workup

  1. customA solution obtained
  2. additionwas added dropwise
  3. customat a room temperature
  4. waitAfter agitation for an hour
  5. concentrationthe reaction mixture was concentrated under a reduced pressure
  6. additionAfter addition of 5 ml of hexane, insoluble materials
  7. filtrationwere filtered off
  8. distillationthe hexane was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-e2b2b835819147bc819b02a84f09debf
Source dataset
uspto-grants-1991_12
Patent number
US05071966

Reaction notes

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