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

HRID 1460726
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HRID 1460726 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-47155312f2894a30a7c5a91dc331dfad
출처 데이터셋
uspto-grants-1991_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05071966

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