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Chlorotrimethylsilane → p-Nitrobenzyl 2-diazo-3-trimethylsilyloxy-3-butenoate

HRID 1460729
Notes
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Reaction equation

HRID 1460729 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].[Br-].[Li+].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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 82050Lithium BromideHCID 53872938HCID 53872938, compound

Product 1

HCID 54029376p-Nitrobenzyl 2-diazo-3-trimethylsilyloxy-3-butenoateYield 98.4%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
40 °C

Procedure

Into 5 ml of dry acetonitrile were suspended 263 mg (1 millimole) of p-nitrobenzyl 2-diazoacetoacetate and 122 mg (1.4 millimoles) of lithium bromide. To the mixture were added 220 μl (1.6 millimoles) of triethylamine and then 190 μl (1.5 millimoles) of trimethylsilyl chloride while agitating under an argon atmosphere at a room temperature. The resultant was heated up to 40° C. and agitated at the same temperature overnight, followed by concentration 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 filtrate was concentrated to dryness under a reduced pressure to give 330 mg (yield 87%) 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. concentrationfollowed by concentration 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 filtrate was concentrated to dryness under a reduced pressure

Sources & evidence

ORD record
ord-7c2b49358fa04611bec0fd72f531689c
Source dataset
uspto-grants-1991_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05071966

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes