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

HRID 1460726Notes

Reaction equation

HRID 1460726 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].[I-].[Na+].C(N(CC)CC)C.[CH3:29][Si:30](Cl)([CH3:32])[CH3:31]>C(#N)C>[N+:1](=[C:3]([C:17]([O:18][Si:30]([CH3:32])([CH3:31])[CH3:29])=[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 98.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Into 5 ml of dry acetonitrile were suspended 263 mg (1 millimole) of p-nitrobenzyl 2-diazoacetoacetate and 210 mg (1.4 millimoles) of sodium iodide. To the mixture were added 220 μl (1.6 millimoles) of triethylamine and then 190 μl (1.5 millimoles) of trimethylsilyl chloride while agitating in an argon atmosphere at a room temperature. After the resulting orange suspension was agitated at a room temperature for an hour, it was concentrated under a reduced pressure. To the residue was added 20 ml of dry hexane, and the resultant was agitated for 30 min. at a room temperature. Insoluble materials were removed by filtration and the hexane solution was concentrated to dryness under a reduced pressure to give 330 mg (yield 98 %) of the desired compound in a yellow solid. The physical properties of the product were in agreement with those of the product obtained in Example 1.

Workup

  1. concentrationit was concentrated under a reduced pressure
  2. additionTo the residue was added 20 ml of dry hexane
  3. stirringthe resultant was agitated for 30 min. at a room temperature
  4. customInsoluble materials were removed by filtration
  5. concentrationthe hexane solution was concentrated to dryness under a reduced pressure

Sources & evidence

ORD record
ord-47155312f2894a30a7c5a91dc331dfad
Source dataset
uspto-grants-1991_12
Patent number
US05071966

Reaction notes

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